Substituted pyridines/pyrimidines, their preparation and their use as pesticides

ABSTRACT

The present invention relates to novel substituted pyridines/pyrimidines of the formula I                    
     where 
     A is CH or N; 
     X is NH, O or S(O) q  where q is 0, 1 or 2; 
     Y 1 , Y 2  and Y 3  independently of one another are a group of the formula —O—, —CO—, —CNR 6 —, —S(O) r — or —N(O) l R 6 — where l is 0 or 1 and where r is 0, 1 or 2, or a group of the formula CR 7 R 8 , or 
     Y 1  or Y 3  replace a direct bond; 
     Z is a direct bond, NR 9 , O, S(O) s  where s is 0, 1 or 2, OSO 2 , SO 2 O, NR 10 SO 2 , SO 2 NR 11 , SiR 12 R 13  or                    
      where 
     U is a direct bond, NR 14  or O; 
     W is oxygen or sulfur; 
     V is a direct bond, NR 15  or oxygen; 
     m and n and 0, 1, 2, 3 or 4; where the radicals R 1  to R 15  have the meaning given in the description, to processes for their preparation, to their use as pesticides, fungicides and ovicides and to their use as veterinary medicaments.

This application is a continuation of application U.S. Ser. No.08/843,151, filed Apr. 11, 1997 now abandoned.

The invention relates to novel substituted pyridines/pyrimidines, toprocesses for their preparation, and to their use as pesticides,fungicides and ovicides.

It has already been disclosed that certain cycloalkylamino and -alkoxyheterocycles have a fungicidal, acaricidal and insecticidal activity(U.S. Pat. No. 5,571,815). However, the biological activity of thesecompounds is not satisfactory for all exemples of use, in particularwhen low rates and concentrations are applied.

There have been found novel substituted pyridines/pyrimidines of theformula I

in which the radicals and groups are as defined below and which arehighly suitable for controlling animal pests such as insects, arachnids,nematodes, helminths and molluscs and eggs of these, for controllingendo- and ectoparasites in the field of veterinary medicine and forcontrolling harmful fungi while showing good plant tolerance andfavorable toxicity to warm-blooded species.

The invention therefore relates to compounds of the formula I in which

R¹ is hydrogen, halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl or(C₃-C₅)-cycloalkyl;

R² and R³ are identical or different and are in each case hydrogen,(C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-haloalkenyl,(C₂-C₄)-alkynyl, (C₂-C₄)-haloalkynyl,tri-(C₁-C₄)-alkylsilyl-(C₂-C₄)-alkynyl, (C₁-C₄)-alkoxy,(C₁-C₄)-haloalkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,(C₁-C₄)-haloalkoxy-(C₁-C₄)-alkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-haloalkyl,(C₁-C₄)-haloalkoxy-(C₁-C₄)-haloalkyl, halogen, hydroxyl,(C₁-C₄)-hydroxyalkyl, (C₁-C₄)-alkanoyl, (C₁-C₄)-alkanoyl-(C₁-C₄)-alkyl,(C₂-C₄)-haloalkanoyl, (C₃-C₅)-cycloalkyl, (C₄-C₅)-cycloalkenyl,(C₃-C₅)-cycloalkoxy, (C₃-C₅)-halocycloalkyl, (C₄-C₅)-halocycloalkenyl,cyano, (C₁-C₄)-cyanoalkyl, nitro, (C₁-C₄)-nitroalkyl, thiocyano,(C₁-C₄)-thiocyanoalkyl, (C₁-C₄)-alkoxycarbonyl,(C₁-C₄)-alkoxycarbonyl-(C₁-C₄)-alkyl, (C₁-C₄)-haloalkoxycarbonyl,(C₁-C₄)alkanoyloxy-(C₁-C₄)-alkyl, (C₁-C₄)-alkylthio(C₁-C₄)-alkylthio-(C₁-C₄)-alkyl, (C₁-C₄)-haloalkylthio,(C₁-C₄)-alkylsulfinyl, (C₁-C₄)-haloalkylsulfinyl, (C₁-C₄)-alkylsulfonylor (C₁-C₄)-haloalkylsulfonyl; or

R² and R³ together with the carbon atoms to which they are bonded forman unsaturated 5- or 6-membered carbocyclic ring which, if it is a5-membered ring, can contain an oxygen or sulfur atom instead of CH₂ orwhich, if it is a 6-membered ring, can contain one or two nitrogen atomsinstead of one or two CH units and which is optionally substituted by 1,2 or 3 identical or different radicals R²⁷, or

R² and R³ together with the carbon atoms to which they are bonded form asaturated 5-, 6- or 7-membered carbocyclic ring which can contain oxygenand/or sulfur instead of one or two CH₂ groups and which is optionallysubstituted by 1, 2 or 3 (C₁-C₄)-alkyl groups;

A is CH or N;

X is NH, O or S(O)_(q) where q is 0, 1 or 2;

Y¹, Y² and Y³ independently of one another are a group of the formula—O—, —CO—, —CNR⁶—, —S(O)_(r)—, —N(O)_(l)R⁶— or CR⁷R⁸ where r is 0, 1 or2 and l is 0 or 1 or

Y¹ or Y³ replace a direct bond;

R⁴ is hydrogen or (C₁-C₄)-alkyl;

m is 0, 1, 2, 3 or 4, preferably 1 or 2;

n is 0, 1, 2, 3 or 4, preferably 1 or 2;

Z is a direct bond, NR⁹, O, S(O)_(s) where s is 0, 1 or 2, OSO₂, SO₂O,NR¹⁰SO₂, SO₂NR¹¹, SiR¹²R¹³, U¹P(W¹)V¹V² or

 where

U¹, U² independently of one another are a direct bond, NR¹⁴ or O;

W¹, W² independently of one another are oxygen or sulfur, preferablyoxygen;

V¹, V², V³ are identical or different and are a direct bond, NR¹⁵ oroxygen, where

R⁹, R¹⁰, R¹¹, R¹⁴ and R¹⁵ are identical or different and are in eachcase hydrogen, alkyl, alkoxy, alkanoyl or cycloalkyl;

R⁵ radicals are substituents which are independent of one another andare halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl,cycloalkenyl and it being possible for one or more, preferably up tothree, non-adjacent saturated carbon units in the last-mentioned 5radicals to be replaced by a carbonyl group or by hetero atom units suchas oxygen, S(O)_(x) where x is 0, 1 or 2, NR¹⁶ or SiR¹⁷R¹⁸, and it beingpossible for these last-mentioned 5 radicals, with or without theabovementioned variations, to be optionally substituted by one or more,preferably up to three, in the case of fluorine up to the maximum numberof, identical or different radicals D¹R¹⁹, or

R⁵ can be aryl or heterocyclyl, it being possible for these two radicalsto be unsubstituted or to be substituted by up to three, in the case offluorine also up to the maximum number of, identical or differentradicals D²R²⁰, or two adjacent radicals

Z—R⁵ together with the carbon atoms to which they are attached can forma fused cycle having 4 to 6 ring atoms which is carbocyclic or containshetero ring atoms selected from the group consisting of O, S and N andwhich is unsubstituted or substituted by one or more radicals selectedfrom the group consisting of halogen, (C₁-C₄)-alkyl and oxo, or

R⁹, R¹⁰, R¹¹, R¹⁴ or R¹⁵ independently of one another together with theR⁵ which is attached to Z can form a 4- to 8-membered ring system inwhich one or two CH₂ groups, preferably one CH₂ group, can be replacedby hetero atom units such as oxygen, S(O)_(t) where t is 0, 1 or 2 orNR²⁵, where

R⁶ is hydrogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₂-C₄)-alkenyl,(C₂-C₄)-haloalkenyl, (C₂-C₄)-alkynyl, (C₂-C₄)-haloalkynyl,(C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio,(C₁-C₄)-haloalkylthio, (C₁-C₄)-alkanoyl, (C₂-C₄)-haloalkanoyl,(C₃-C₅)-cycloalkyl, (C₁-C₄)-alkylsulfonyl, (C₁-C₄)-haloalkylsulfonyl(C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₄)-alkoxycarbonyl;

R⁷ and R⁸ independently of one another are hydrogen, hydroxyl, halogen,cyano, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₂-C₄)-alkenyl,(C₂-C₄)-haloalkenyl, (C₂-C₄)-alkynyl, (C₂-C₄)-haloalkenyl,(C₃-C₅)-cycloalkyl, (C₁-C₄)-alkanoyl, (C₁-C₄)-haloalkanoyl,(C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio or(C₁-C₄)-haloalkylthio;

R¹² and R¹³ independently of one another are (C₁-C₄)-alkyl or phenyl,preferably methyl;

R¹⁶ is hydrogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy or (C₁-C₄)-alkanoyl;

R¹⁷ and R¹⁸ independently of one another are (C₁-C₄)-alkyl, preferablymethyl;

D¹ and D² are in each case independent of one another and are a directbond, oxygen, S(O)_(k), SO₂O, OSO₂, CO, OCO, COO, NR²¹, SO₂NR²¹,NR²¹SO₂, ONR²¹, NR²¹O, NR²¹CO, CONR²¹ or SiR²²R²³ and k is 0, 1 or 2,where

R²¹ radicals independently of one another are hydrogen, (C₁-C₄)-alkyl,(C₁-C₄)-alkanoyl or (C₃-C₅)-cycloalkyl;

R²² and R²³ independently of one another are (C₁-C₄)-alkyl;

R¹⁹ and R²⁰ independently of one another are hydrogen, cyano, nitro,halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl,alkoxyalkyl, haloalkoxyalkyl, alkylthioalkyl, haloalkylthioalkyl,cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl, aryl,heterocyclyl, arylalkyl or heterocyclylalkyl, it being possible for thecycloaliphatic, aromatic or heterocyclic ring systems in thelast-mentioned 8 radicals to be unsubstituted or to be provided with upto three, in the case of fluorine also up to the maximum number of,identical or different substituents R²⁴, or

R¹⁹ and R²⁰, attached to the same carbon atom, together are an oxogroup; where

R²⁴ radicals independently of one another can be (C₁-C₄)-alkyl,(C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, cyano, nitro orhalogen;

R²⁵ independently of one another can be hydrogen, (C₁-C₈)-alkyl,(C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-alkylthio,(C₃-C₅)-cycloalkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-alkynyl, (C₁-C₄)-alkanoyl,(C₁-C₄)-haloalkanoyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, phenyl-(C₁-C₄)-alkylor phenyl, it being possible for the phenyl groups independently of oneanother to be unsubstituted or provided with up to three, in the case offluorine also up to the maximum number of, identical or differentsubstituents R²⁶, where

R²⁶ substituents independently of one another can be (C₁-C₄)-alkyl,(C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-alkylthio, halogen or cyano,and

R²⁷ radicals independently of one another are (C₁-C₄)-alkyl,(C₁-C₄)-haloalkyl, preferably trifluoromethyl, halogen, (C₁-C₄)-alkoxyor (C₁-C₄)-haloalkoxy;

and salts thereof, preferably acid addition salts;

in particular those compound where

R⁵ radicals are substituents which are independent of one another andare halogen, cyano, nitro, (C₁-C₂₀)-alkyl, (C₂-C₂₀)-alkenyl,(C₂-C₂₀)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl and one ormore, preferably up to three, non-adjacent saturated carbon units in thelast-mentioned 5 radicals can be replaced by a carbonyl group or byhetero atom units such as oxygen, S(O)_(x) where x is 0, 1 or 2, NR¹⁶ orSiR¹⁷R¹⁸ and it being possible for these last-mentioned 5 radicals, withor without the abovementioned variations, to be optionally substitutedby one or more, preferably up to three, in the case of fluorine up tothe maximum number of, identical or different radicals D¹R¹⁹, or

R⁵ can be aryl or heterocyclyl, it being possible for these two radicalsto be unsubstituted or to be substituted by up to three, in the case offluorine also up to the maximum number of, identical or differentradicals D²R²⁰, or two adjacent radicals

Z—R⁵ together with the carbon atoms to which they are attached can forma fused cycle having 4 to 6 ring atoms which is carbocyclic or containshetero ring atoms selected from the group consisting of O, S and N andwhich is unsubstituted or substituted by one or more radicals selectedfrom the group consisting of halogen, (C₁-C₄)-alkyl and oxo, or

R⁹, R¹¹ or R¹⁵ independently of one another together with the R⁵attached to Z can form a 4- to 8-membered ring system in which one ortwo CH₂ groups, preferably one CH₂ group, can be replaced by hetero atomunits such as oxygen, S(O)_(t) where t is 0, 1 or 2 or NR²⁵, where

R¹⁶ is hydrogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy or (C₁-C₄)-alkanoyl;

R¹⁷ and R¹⁸ independently of one another are (C₁-C₄)-alkyl, preferablymethyl; D¹ and D² are in each case independent of one another and are adirect bond, oxygen, S(O)_(k), SO₂O, OSO₂, CO, OCO, COO, NR²¹, SO₂NR²¹,NR²¹SO₂, ONR²¹, NR²¹O, NR²¹CO, CONR²¹ or SiR²²R²³ and k is 0, 1 or 2,where

R²¹ radicals independently of one another are hydrogen, (C₁-C₄)-alkyl,(C₁-C₄)-alkanoyl or (C₃-C₅)-cycloalkyl;

R²² and R²³ independently of one another are (C₁-C₄)-alkyl;

R¹⁹ and R²⁰ independently of one another are hydrogen, cyano, nitro,halogen, (C₁-C₈)-alkyl, (C₁-C₈)-haloalkyl, (C₂-C₈)-alkenyl,(C₂-C₈)-haloalkenyl, (C₂-C₈)-alkynyl, (C₂-C₈)-haloalkynyl,(C₁-C₈)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₈)-haloalkoxy-(C₁-C₄)-alkyl,(C₁-C₈)-alkylthio-(C₁-C₄)-alkyl, (C₁-C₈)-haloalkylthio-(C₁-C₄)-alkyl,(C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl,(C₃-C₈)-cycloalkyl-(C₁-C₄)-alkyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkyl,aryl, heterocyclyl, aryl-(C₁-C₄)-alkyl or heterocyclyl-(C₁-C₄)-alkyl,where, in the last-mentioned 8 radicals, the cycloaliphatic, aromatic orheterocyclic ring systems can be unsubstituted or provided with up tothree, in the case of fluorine also up to the maximum number of,identical or different substituents R²⁴, or

R¹⁹ and R²⁰, attached to the same carbon atom, together are an oxogroup, where

R²⁴ can be (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy,(C₁-C₄)-haloalkoxy, cyano, nitro or halogen;

R²⁵ radicals are hydrogen, (C₁-C₈)-alkyl, (C₁-C₄)-haloalkyl,(C₁-C₄)-alkoxy, (C₁-C₄)-alkylthio, (C₃-C₅)-cycloalkyl, (C₂-C₄)-alkenyl,(C₂-C₄)-alkynyl, (C₁-C₄)-alkanoyl, (C₂-C₄)-haloalkanoyl,(C₂-C₄)-alkoxyalkyl, phenyl-(C₁-C₄)-alkyl or phenyl and the phenylgroups can be unsubstituted or provided with up to three, in the case offluorine also up to the maximum number of, identical or differentsubstituents R²⁶, where

R²⁶ can be (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy,(C₁-C₄)-alkylthio, halogen or cyano.

Preferred compounds of the formula I are those in which

R¹ is hydrogen, chlorine or fluorine;

R² is (C₁-C₄)-alkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-alkynyl,tri-(C₁-C₄)-alkylsilyl-(C₂-C₄)-alkynyl, (C₁-C₄)-haloalkyl, cyclopropyl,halocyclopropyl, methoxymethyl or cyano;

R³ is hydrogen, halogen, methyl, ethyl, ethenyl, ethynyl, methoxy,ethoxy, cyano, trifluoromethyl, fluoromethylthio or methoxycarbonyl; or

R² and R³ together with the carbon atoms to which they are bonded forman optionally substituted unsaturated 5- or 6-membered ring which, inthe case of a 5-membered ring, can contain a sulfur atom instead of aCH₂ unit; or

R² and R³ together with the carbon atoms to which they are bonded form asaturated 5- or 6-membered ring which can contain a sulfur or an oxygenatom instead of a CH₂ unit;

A is CH or N;

X is NH or oxygen;

Y¹, Y² and Y³ independently of one another are a group of the formula—O—, —S(O)_(r)—, —N(O)_(l)R⁶— or CR⁷R⁸ where r is =0, 1 or 2 and l is 0or 1; or

Y¹ or Y² replace a direct bond;

R₄ is hydrogen;

m is 1 or 2;

n is 1 or 2;

Z is a direct bond, NR⁹, O, S(O)_(s) where s is 0, 1 or 2, or OSO₂,SO₂O, NR¹⁰SO₂, SO₂NR¹¹, SiR¹²R¹³, U¹ P(W¹)V¹V² or

 where

U¹, U² independently of one another are a direct bond, NR¹⁴ or O;

W¹, W² are oxygen;

V¹, V², V³ independently of one another are a direct bond, NR¹⁵ oroxygen; where

R⁶ radicals independently of one another can be (C₁-C₄)-alkyl or(C₁-C₄)-alkanoyl;

R⁷ and R⁸ independently of one another are hydrogen, halogen or(C₁-C₄)-alkyl, and

R⁹, R¹⁰, R¹¹, R¹⁴ and R¹⁵ are identical or different and are in eachcase hydrogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-alkanoyl or(C₃-C₅)-cycloalkyl;

in particular those compounds in which

R¹ is hydrogen or fluorine;

R² is methyl, ethyl, propyl, isopropyl, (C₁-C₂)-fluoroalkyl ormethoxymethyl;

R³ is halogen, methyl, ethyl, ethenyl, ethynyl, methoxy, ethoxy,trifluoromethyl, fluoromethylthio, methoxycarbonyl or cyano; or

R² and R³ together with the ring system to which they are bonded formthe quinazoline or quinoline system, which can be substituted in thecarbocyclic moiety by fluorine; or

R² and R³ together with the carbon atoms to which they are bonded form asaturated 6-membered ring which can contain an oxygen or sulfur atominstead of a CH₂ group;

A is CH or N;

X is NH or oxygen;

Y¹, Y² and Y³ are a group of the formula —O—, or —S(O)_(r)—, where r is0, 1 or 2, or a group of the formula CR⁷R⁸, or Y¹ or Y³ replace a directbond, where

R⁷ and R⁸ independently of one another are hydrogen or methyl.

Especially preferred are those compounds of the formula I in which

R¹ is hydrogen;

R² is ethyl, propyl, isopropyl, 1 -fluoroethyl or methoxymethyl;

R³ is fluorine, chlorine, bromine, cyano, methoxy, ethenyl or ethynyl;or, in the event that A is nitrogen,

R² and R³ together with the ring system to which they are bonded formthe quinazoline system which can be substituted by a fluorine atom.

Most preferred are those compounds of the formula I where

R¹ is hydrogen;

R² is ethyl or methoxymethyl;

R³ is fluorine, chlorine, bromine or methoxy;

R⁵ radicals are substituents which are independent of one another andare halogen, cyano, nitro, (C₁-C₈)-alkyl, (C₂-C₈)-alkenyl,(C₂-C₈)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl and it ispossible for one or more, preferably up to three, non-adjacent saturatedcarbon units in the last-mentioned 5 radicals to be replaced by acarbonyl group or by hetero atom units such as oxygen, S(O)_(x) where xis 0, 1 or 2, NR¹⁶ or SiR¹⁷R¹⁸, and these last-mentioned 5 radicals,with or without the abovementioned variations, can be optionallysubstituted by one or more, preferably up to three, in the case offluorine up to the maximum number of, identical or different radicalsD¹R¹⁹, or

R⁵ can be aryl or heterocyclyl, it being possible for these two radicalsto be unsubstituted or to be substituted by up to three, in the case offluorine also up to the maximum number of, identical or differentradicals D²R²⁰, or two adjacent radicals

Z—R⁵ together with the carbon atoms to which they are attached can forma fused cycle having 4 to 6 ring atoms which is carbocyclic or containshetero ring atoms selected from the group consisting of O, S and N andwhich is unsubstituted or substituted by one or more radicals selectedfrom the group consisting of halogen, (C₁-C₄)-alkyl and oxo, or

R¹¹ or R¹⁵ independently of one another together with the R⁵ which isattached to Z can form a 4- to 8-membered ring system in which one ortwo CH₂ groups, preferably one CH₂ group, can be replaced by hetero atomunits such as oxygen, S(O)_(t) where t is 0, 1 or 2 or NR²⁵, where

R¹⁶ radicals independently of one another are hydrogen, (C₁-C₄)-alkyl,(C₁-C₄)-alkoxy or (C₁-C₄)-alkanoyl, and

R¹⁷ and R¹⁸ independently of one another are (C₁-C₄)-alkyl, preferablymethyl;

D¹ and D² are in each case independent of one another and are a directbond, —O—, —S(O)_(k)—, —SO₂O—, —OSO₂—, —CO—, —OCO—, —COO—, —NR²¹—,—SO₂NR²¹—, —NR²¹SO₂—, —ONR²¹—, —NR²¹O—, —NR²¹CO—, —CONR²¹—, and k is =0,1 or 2, and where

R²¹ radicals independently of one another are hydrogen, (C₁-C₄)-alkyl,(C₁-C₄)-alkanoyl or (C₃-C₅)-cycloalkyl;

R¹⁹ and R²⁰ independently of one another are hydrogen, halogen,preferably fluorine, (C₁-C₈)-alkyl, (C₃-C₈)-cycloalkyl, aryl orheterocyclyl, it being possible for the cycloaliphatic, aromatic orheterocyclic ring systems in the last-mentioned three radicals to beunsubstituted or provided with up to three, in the case of fluorine alsoup to the maximum number of, identical or different substituents R²⁴,where

R²⁴ radicals independently of one another can be (C₁-C₄)-alkyl,(C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, cyano, nitro,halogen;

R²⁵ radicals independently of one another are (C₁-C₈)-alkyl,(C₃-C₅)-cycloalkyl, (C₁-C₄)-alkanoyl, (C₂-C₄)-haloalkanoyl,(C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, phenyl-(C₁-C₄)-alkyl or phenyl and thephenyl groups can be unsubstituted or provided with up to three, in thecase of fluorine also up to the maximum number of, identical ordifferent substituents R²⁶, where

R²⁶ radicals independently of one another can be (C₁-C₄)-alkyl,(C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-alkylthio, halogen or cyano;

in particular those compounds where

R⁵ radicals independently of one another are (C₁-C₈)-alkyl in which oneor more, preferably up to three, non-adjacent saturated carbon units canbe replaced by oxygen and which, with or without the abovementionedvariations, can optionally be substituted by one or more, preferably upto three, in the case of fluorine up to the maximum number of, identicalor different radicals D¹R¹⁹, or

R⁵ can be aryl or heterocyclyl, it being possible for these two radicalsto be unsubstituted or substituted by up to three, in the case offluorine also up to the maximum number of, identical or differentradicals D²R²⁰.

In the above formula, “halogen” is to be understood as meaning afluorine, chlorine, bromine or iodine atom;

the term “(C₁-C₄)-alkyl” is to be understood as meaning an unbranched orbranched hydrocarbon radical having 1 to 4 carbon atoms such as, forexample, the methyl, ethyl, propyl, isopropyl, 1-butyl, 2-butyl,2-methylpropyl or tert-butyl radical;

the term “(C₁-C₈)-alkyl” the abovementioned alkyl radicals and also, forexample, the pentyl, 2-methylbutyl, 1,1-dimethylpropyl, hexyl, heptyl,octyl, or 1,1,3,3-tetramethylbutyl radical;

the term “(C₁-C₂₀)-alkyl” the abovementioned alkyl radicals and also,for example, the dodecyl, pentadecyl or eicosyl radical;

the term “(C₁-C₄)-haloalkyl” an alkyl group mentioned under the term“(C₁-C₄)-alkyl” in which one or more hydrogen atoms are replaced by theabovementioned halogen atoms, preferably chlorine and fluorine, such as,for example, the trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl,2,2,2-trifluoroethyl, chloromethyl, fluoromethyl, difluoromethyl or the1,1,2,2-tetrafluoroethyl group;

the term “(C₁-C₂)-fluoroalkyl”, for example, the mono-, di-,trifluoromethyl, 1 -fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl,1,1-difluoroethyl or the 2,2,2-trifluoroethyl group;

the term “cycloalkyl” preferably (C₃-C₈)-cycloalkyl;

the term “cycloalkenyl” preferably (C₃-C₈)-cycloalkenyl;

the term “(C₃-C₅)-cycloalkyl” the cyclopropyl, cyclobutyl or cyclopentylgroup;

the term “(C₃-C₈)-cycloalkyl” the radicals mentioned above under“(C₃-C₅)-cycloalkyl” and also the cyclohexyl, cycloheptyl or cyclooctylradical, but also bicyclic systems such as, for example, the norbornylgroup or the bicyclo[2.2.2]octane radical;

the term “(C₃-C₅)-halocycloalkyl” one of the above-listed(C₃-C₅)-cycloalkyl radicals in which one or more, in the case offluorine optionally also all, hydrogen atoms are replaced by halogen,preferably fluorine or chlorine, such as, for example, the 2,2-difluoro-or 2,2-dichlorocyclopropane group or the fluorocyclopentane radical;

the term “(C₂-C₄)-alkenyl” for example the vinyl, allyl,2-methyl-2-propenyl or 2-butenyl group;

the term “(C₂-C₈)-alkenyl” the radicals mentioned above under“(C₂-C₄)-alkenyl” and, for example, the 2-pentenyl or the 2-octenylgroup;

the term “(C₂-C₂₀)-alkenyl” the radicals mentioned above under“(C₂-C₈)-alkenyl” and also, for example, the 2-decenyl or the2-eicosenyl group;

the term “(C₂-C₄)-haloalkenyl” a (C₂-C₄)-alkenyl group in which some orelse, in the case of fluorine, all hydrogen atoms are replaced byhalogen, preferably fluorine or chlorine,

the term “(C₂-C₈)-haloalkyl” a (C₂-C₈)-alkenyl group in which some, inthe case of fluorine also all, hydrogen atoms are replaced by halogen,preferably fluorine or chlorine;

the term “(C₄-C₅)-cycloalkenyl” the cyclobutenyl or cyclopentenyl group;

the term “(C₄-C₈)-cycloalkenyl” the abovementioned radicals and also,for example, the 1-cyclohexenyl group;

the term “(C₂-C₄)-alkynyl”, for example, the ethynyl, propargyl,2-methyl-2-propynyl, 1-butynyl, 2-butynyl or the 3-butynyl group;

the term “(C₂-C₈)-alkynyl” the radicals mentioned above under“(C₂-C₄)-alkynyl” and also, for example, the 2-pentynyl or the 2-octynylgroup,

the term “(C₂-C₂₀)-alkynyl” the radicals mentioned above under“(C2-C₈)-alkynyl” and also, for example, the 2-decynyl group;

the term “(C₂-C₄)-haloalkynyl” a (C₂-C₄)-alkynyl group in which some, inthe case of fluorine also all, hydrogen atoms are replaced by halogenatoms, preferably fluorine or chlorine, or else the iodoethynyl group;

the term “(C₂-C₈)-haloalkynyl” a (C₂-C₈)-alkynyl group in which some, inthe case of fluorine all, hydrogen atoms are replaced by halogen atoms,preferably fluorine or chlorine;

the term “tri-(C₁-C₄)-alkylsilyl-(C₂-C₄)-alkynyl” preferably thetrimethylsilylethynyl group;

the term “(C₁-C₄)-hydroxyalkyl” for example the hydroxymethyl,1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxy-1-methylethyl or the1-hydroxypropyl group;

the term “(C₁-C₄)-alkanoyl” for example the formyl, acetyl, propionyl,2-methylpropionyl or butyryl group;

the term “(C₂-C₄)-haloalkanoyl” a (C₂-C₄)-alkanoyl group in which some,in the case of fluorine all, hydrogen atoms are replaced by halogenatoms, preferably fluorine or chlorine;

the term “cyano-(C₁-C₄)-alkyl” a cyanoalkyl group whose hydrocarbonradical has the meaning given under the term “(C₁-C₄)-alkyl”;

the term “(C₁-C₄)-alkoxycarbonyl” for example the methoxycarbonyl,ethoxycarbony, propoxycarbonyl, butoxycarbonyl or tert-butoxycarbonylgroup;

the term “(C₁-C₄)-haloalkoxycarbonyl” a (C₁-C₄)-alkoxycarbonyl group inwhich one or more, in the case of fluorine all, hydrogen atoms arereplaced by halogen, preferably fluorine or chlorine;

the term “(C₁-C₄)-alkylthio” an alkylthio group whose hydrocarbonradical has the meaning given under the term “(C₁-C₄)-alkyl”;

the term “(C₁-C₄)-haloalkylthio” a (C₁-C₄)-alkylthio group in which oneor more, in the case of fluorine optionally also all, hydrogen atoms ofthe hydrocarbon radical are replaced by halogen, preferably chlorine orfluorine;

the term “fluoromethylthio” the mono-, di- and trifluoromethylthiogroup;

the term “(C₁-C₄)-alkylsulfinyl” for example the methyl-, ethyl-,propyl-, isopropyl-, butyl-, isobutyl-, sec-butyl- or tert-butylsulfinylgroup;

the term “(C₁-C₄)-alkylsulfonyl” for example the methyl-, ethyl-,propyl-, isopropyl-, butyl-, isobutyl-, sec-butyl- or tert-butylsulfonylgroup;

the terms “(C₁-C₄)-haloalkylsulfinyl” and “(C₁-C₄)-haloalkylsulfonyl”(C₁-C₄)-alkylsulfinyl- and -sulfonyl radicals having the meanings givenabove in which one or more, in the case of fluorine optionally also all,hydrogen atoms of the hydrocarbon radical are replaced by halogen,preferably chlorine or fluorine;

the term “(C₁-C₄)-alkoxy” an alkoxy group whose hydrocarbon radical hasthe meaning given under the term “(C₁-C₄)-alkyl”;

the term “(C₁-C₄)-haloalkoxy” a haloalkoxy group whose halohydrocarbonradical has the meaning given under the term “(C₁-C₄)-haloalkyl”;

the term “(C₁-C₄)-alkoxy-(C₁-C₄)-alkyl” for example the 1-methoxyethyl,2-methoxyethyl, 2-ethoxyethyl, methoxymethyl, ethoxymethyl,3-methoxypropyl or the 4-butoxybutyl group;

the terms “(C₁-C₄)-haloalkoxy-(C₁-C₄)-alkyl”,“(C₁-C₄)-alkoxy-(C₁-C₄)-haloalkyl” and“(C₁-C₄)-haloalkoxy-(C₁-C₄)-haloalkyl” (C₁-C₄)-alkoxy-(C₁-C₄)-alkylradicals having the meanings given above in which one or more, in thecase of fluorine optionally also all, hydrogen atoms in the relevanthydrocarbon moieties are replaced by halogen, preferably chlorine orfluorine;

the term “(C₁-C₄)-alkylthio-(C₁-C₄)-alkyl” for example methylthiomethyl,ethylthiomethyl, propylthiomethyl, 2-methylthioethyl, 2-ethylthioethylor 3-methylthiopropyl;

the term “(C₃-C₅)-cycloalkoxy” the cyclopropoxy, cyclobutoxy orcyclopentoxy group;

the term “(C₃-C₈)-cycloalkyl-(C₁-C₄)-alkyl” for example acyclopropylmethyl, a cyclopentylethyl or a cyclohexylmethyl group;

the term “(C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkyl” for example acyclobutenylmethyl group, a cyclopenten-1-ylethyl group or acyclohexene-3-ylmethyl group;

the term “phenyl-(C₁-C₄)-alkyl” preferably benzyl;

the term “aryl-(C₁-C₄)-alkyl” for example the benzyl, the 2-phenylethyl,the 1-phenylethyl, the 1-methyl-1-phenylethyl group, the 2-phenylpropyl,the 4-phenylbutyl group, the 2-methyl-2-phenylethyl group or the1-methyl- or 2-methylnaphthyl group;

the term “heterocyclyl-(C₁-C₄)-alkyl” for example the thienylmethyl,pyridylmethyl, furfuryl-, tetrahydrofurfuryl-, tetrahydropyranylmethylor the 1,3-dioxolan-2-ylmethyl group;

the term “aryl” a carbocyclic aromatic radical having preferably 6 to14, in particular 6 to 12, carbon atoms such as, for example, phenyl,naphthyl or biphenyl, preferably phenyl;

the term “heterocyclyl” a heteroaromatic or heteroaliphatic ring system,“heteroaromatic ring system” to be understood as meaning an aryl radicalin which at least one CH group is replaced by N and/or at least twoadjacent CH groups are replaced by S, NH or O, for example a radical ofthiophene, furan, pyrrole, thiazole, oxazole, imidazole, isothiazole,isoxazole, pyrazole, 1,3,4-oxadiazole, 1,3,4-thiadiazole,1,3,4-triazole, 1,2,4-oxadiazole, 1,2,4-thiadiazole, 1,2,4-triazole,1,2,3-triazole, 1,2,3,4-tetrazole, benzo[b]thiophene, benzo[b]furan,indole, benzo[c]thiophene, benzo[c]furan, isoindole, benzoxazole,benzothiazole, benzimidazole, benzisoxazole, benzisothiazole,benzopyrazole, benzothiadiazole, benzotriazole, dibenzofuran,dibenzothiophene, carbazole, pyridine, pyrazine, pyrimidine, pyridazine,1,3,5-triazine, 1,2,4-triazine, 1,2,4,5-triazine, quinoline,isoquinoline, quinoxaline, quinazoline, cinnoline, 1,8-naphthyridine,1,5-naphthyridine, 1,6-naphthyridine, 1,7-naphthyridine, phthalazine,pyridopyrimidine, purine, pteridine or 4H-quinolizine;

and the term “heteroaliphatic ring system” a (C₃-C₈)-cycloalkyl radicalin which at least one carbon unit is replaced by O, S or a group NR¹¹and R¹¹ is hydrogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy or aryl.

What has been explained above applies analogously to homologs orradicals derived therefrom.

The present invention relates to the compounds of the formula I in theform of the free bases or of a salt, preferably an acid addition salt.Acids which can be used for salt formation are, for example, inorganicacids such as hydrochloric acid, hydrobromic acid, nitric acid, sulfuricacid, phosphoric acid, or organic acids such as formic acid, aceticacid, propionic acid, malonic acid, oxalic acid, fumaric acid, adipicacid, stearic acid, oleic acid, methanesulfonic acid, benzenesulfonicacid or toluenesulfonic acid.

Some of the compounds of the formula I have one or more asymmetriccarbon atoms or stereoisomers on double bonds. Enantiomers ordiastereomers are therefore possible. The scope of the invention extendsboth to the pure isomers and also to mixtures of these. The diastereomermixtures can be separated into the components by customary methods, forexample by selective crystallization from suitable solvents or bychromatography. Racemates can be resolved by customary methods to givethe enantiomers, for example by salt formation with an optically activeacid, separation of the diastereomeric salts and liberation of the pureenantiomers by means of a base.

The invention furthermore relates to a process for the preparation ofcompounds of the formula I which comprises reacting a compound of theformula II

where A, R¹, R² and R³ have the meanings given above for formula I and Lis a leaving group, for example halogen, alkylthio, alkanesulfonyloxy orarylsulfonyloxy, alkylsulfonyl or arylsulfonyl, with a nucleophile ofthe formula III

where X, Y¹, Y², Y³, Z, R⁴, R⁵, m and n have the meanings given abovefor formula I and, if appropriate, further derivatizing the nitrogenheterocycle or the side chain(s) R⁵ in the compounds of the formula Iobtained in this or another manner.

The above-described substitution reaction is known in principle. Theleaving group L can be varied within wide limits and can be, forexample, a halogen atom such as fluorine, chlorine, bromine or iodine,or alkylthio such as methyl- or ethylthio, or alkanesulfonyloxy such asmethane-, trifluoromethane- or ethanesulfonyloxy or arylsulfonyloxy,such as benzenesulfonyloxy or toluenesulfonyloxy, or alkylsulfonyl suchas methyl- or ethylsulfonyl, or arylsulfonyl such as phenyl- ortoluenesulfonyl.

The abovementioned reaction is carried out in a temperature range offrom 20 to 150° C., expediently in the presence of a base and, ifappropriate, in an inert organic solvent such as, for example,N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide,N-methylpyrrolidin-2-one, dioxane, tetrahydrofuran,4-methyl-2-pentanone, methanol, ethanol, butanol, ethylene glycol,ethylene glycol dimethyl ether, toluene, chlorobenzene or xylene.Mixtures of the abovementioned solvents can also be used.

In the event that X is oxygen, examples of suitable bases are alkalimetal carbonates, alkali metal hydrogen carbonates, alkali metal amides,alkali metal hydrides, alkaline earth metal carbonates, alkaline earthmetal hydrogen carbonates, alkaline earth metal amides or alkaline earthmetal hydrides such as sodium carbonate, sodium hydrogen carbonate,potassium carbonate, sodium amide or sodium hydride, and in the eventthat X is NH, examples of suitable bases are alkali metal carbonates,alkali metal hydrogen carbonates, alkali metal hydroxides, alkali metalamides, alkali metal hydrides, alkaline earth metal carbonates, alkalineearth metal hydrogen carbonates, alkaline earth metal hydroxides,alkaline earth metal amides or alkaline earth metal hydrides such assodium carbonate, sodium hydrogen carbonate, potassium carbonate, sodiumhydroxide, sodium amide or sodium hydride or organic bases such astriethylamine or pyridine. A second equivalent of an amine of theformula III can also be employed as auxiliary base.

Most of the compounds of the formula II which are required as startingmaterials are known from the literature or can be prepared analogouslyto known methods (cf. EP 370 391, EP 470 600, DOS 43 31 179, DOS 44 04702).

To prepare the nucleophiles of the formula III, suitably substitutedketones of the formula IV are used as starting materials and areconverted into the corresponding amines by reductive amination (H₂, NH₃,metal catalyst or ammonium acetate/sodium cyanoborohydride orLeuckart-Wallach reduction) or into the corresponding alcohols byreduction with a complex metal hydride.

Furthermore, the nucleophiles of the formula III where X=NH can beprepared by reducing an oxime or imine or by subjecting an alkyl halideor alkyl tosylate to a Gabriel reaction or to a Mitsunobu reaction withphthalimide and subsequent hydrazinolysis. Equally, these nucleophilescan be synthesized by reacting an alkyl halide or alkyl tosylate with ametal azide and reducing the azide with a suitable reducing agent, forexample a complex metal hydride, hydrogen in the presence of ahydrogenation catalyst or phosphine or phosphite. Regarding thepreparation of the 2-aminoindenes, the following synthesis route is alsopossible: D. E. Nichols, W. K. Brewster, M. P. Johnson, R. Overlenderand R. U. Riggs, J. Med. Chem. 1990, 33, 703. 2-Aminochromanes are alsoobtainable via other routes (cf. WO 90/12795).

The ketones of the formula IV

are commercially available, known from the literature or can besynthesized analogously to known processes:

J. J. Sims, L. H. Selman, M. Cadogan, Org. Synth. 1971, 61,109;

S. Lee, S. P. Frescas, O. E. Nichols, Synth. Commun. 1995, 2775;

G. D. Johnson, Org. Synth. 1963, IV, 900;

D. Hackle, I. M. Lockhardt, M. Wright, J. Med. Chem. 1969, 12, 277;

R. J. Heffner, M. M. Joullie, Synth. Commun. 1991, 2231;

Krollpfeiffer, Schulze, Chem. Ber. 1923, 56, 1822.

The active substances are well tolerated by plants and have a favorabletoxicity to warm-blooded species and are suitable for controlling animalpests, in particular insects, arachnids, helminths and molluscs andtheir eggs, very especially preferably for controlling insects andarachnids found in agriculture, in livestock breeding, in forests, inthe protection of stored products and materials and in the hygienesector. They are effective against normally sensitive and resistantspecies and all or some developmental stages. The abovementioned pestsinclude:

From the order of the Acarina, for example Acarus siro, Argas spp.,Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptrutaoleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalommaspp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp.,Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp.,Eotetranychus spp., Oligonychus spp., Eutetranychus spp.

From the order of the Isopoda, for example, Oniscus asselus, Armadiumvulgar, Porcellio scaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Chilopoda, for example, Geophilus carpophagus,Scutigera spp.

From the order of the Symphyla, for example, Scutigerella immaculata.

From the order of the Thysanura, for example, Lepisma saccharina.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Orthoptera, for example, Blatta orientalis,Periplaneta americana, Leucophaea madeirae, Blatella germanica, Achetadomesticus, Gryllotalpa spp., Locusta migratoria migratorioides,Melanoplus differentialis, Schistocerca gregaria.

From the order of the Isoptera, for example, Reticulitermes spp.

From the order of the Anoplura, for example, Phylloxera vastatrix,Pemphigus spp., Pediculus humanus corporis, Haematopinus spp.,Linognathus spp.

From the order of the Mallophaga, for example, Trichodectes pp.,Damalinea spp.

From the order of the Thysanoptera, for example, Hercinothripsfemoralis, Thrips tabaci.

From the order of the Heteroptera, for example, Eurygaster spp.,Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodniusprolixus, Triatoma spp.

From the order of the Homoptera, for example, Aleurodes brassicae,Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicorynebrassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosomalanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp.,Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelus bilobatus,Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphaxstriatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotushederae, Pseudococcus spp., Psylla spp.

From the order of the Lepidoptera, for example, Pectinophoragossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletisblancardella, Hyponomeuta padella, Plutella maculipennis, Malacosomaneustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrixthurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltiaspp., Earias insulana, Heliothis spp., Laphygma exigua, Mamestrabrassicae, Panolis flammea, Prodenia litura, Spodoptera spp.,Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyraustanubilalis, Ephestia kuehniella, Galleria mellonella, Cacoecia podana,Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homonamagnanima, Tortrix viridana.

From the order of the Coleoptera, for example, Anobium punctatum,Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus,Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedoncochleariae, Diabrotica spp., Psylloides chrysocephala, Epilachnavarivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonumus spp.,Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus,Ceuthorrynchus assimilis, Hypera postica, Dermestes spp., Trogoderma,Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinusspp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebriomolitor, Agriotes spp., Conoderus spp., Melolontha melolontha,Amphimallon solstitialis, Costelytra zealandica.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampaspp., Lasius spp., Monomorium pharaonis, Vespa spp.

From the order of the Diptera, for example, Aedes spp., Anopheles spp.,Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphoraerythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp.,Gastrophilus spp., Hypobosca spp., Stomoxys spp., Oestrus spp.,Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinellafrit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae,Tipula paludosa.

From the order of the Siphonaptera, for example, Xenopsylla cheopsis,Ceratophyllus spp.

From the order of the Arachnida, for example, Scorpio maurus,Latrodectus mactans.

From the class of the helminths, for example, Haemonchus,Trichostrongulus, Ostertagia, Cooperia, Chabertia, Strongyloides,Oesophagostomum, Hyostrongulus, Ancylostoma, Ascaris and Heterakis andalso Fasciola.

From the class of the gastropods, for example, Deroceras spp., Arionspp., Lymnaea spp., Galba spp., Succinea spp., Biomphalaria spp.,Bulinus spp., Oncomelania spp.

From the class of the bivalves, for example, Dreissena spp.

The plant-parasitic nematodes which can be controlled according to theinvention include, for example, the root-parasitic soil nematodes suchas, for example, those from the genera Meloidogyne (root-knot nematodes,such as Meloidogyne incognita, Meloidogyne hapla and Meloidogynejavanica), Heterodera and Globodera (cyst-forming nematodes, such asGlobodera rostochiensis, Globodera pallida, Heterodera trifolii) andfrom the genera Radopholus, such as Radopholus similis, Pratylenchus,such as Pratylenchus neglectus, Pratylenchus penetrans and Pratylenchuscurvitatus; Tylenchulus, such as Tylenchulus semipenetrans,Tylenchorhynchus, such as Tylenchorhynchus dubius and Tylenchorhynchusclaytoni, Rotylenchus, such as Rotylenchus robustus, Heliocotylenchus,such as Haliocotylenchus multicinctus, Belonoaimus, such as Belonoaimuslongicaudatus, Longidorus, such as Longidorus elongatus, Trichodorus,such as Trichodorus primitivus and Xiphinema, such as Xiphinema index.

Furthermore, the compounds according to the invention can be used forcontrolling the nematode genera Ditylenchus (stem parasites, such asDitylenchus dipsaci and Ditylenchus destructor), Aphelenchoides (foliarnematodes, such as Aphelenchoides ritzemabosi) and Anguina (flower andleaf-gall nematodes, such as Anguina tritici).

The invention also relates to compositions, in particular toinsecticidal, acaricidal and ovicidal compositions, which comprise thecompounds of the formula I in addition to suitable formulationauxiliaries.

The compositions according to the invention comprise the activeingredients of the formula I in a concentration range of from 0.00000001to 95% by weight, preferably from 1 to 95% by weight.

They can be formulated in various ways, depending on the prevailingbiological and/or chemico-physical parameters. The followingformulations are therefore possible:

Wettable powders (WP), emulsifiable concentrates (EC), aqueous solutions(SL), emulsions, sprayable solutions, oil- or water-based dispersions(SC), suspoemulsions (SE), dusts (DP), seed-treatment products, granulesin the form of microgranules, spray granules, coated granules andadsorption granules, water-dispersible granules (WG), ULV formulations,microcapsules, waxes or baits.

These individual types of formulation are known in principle and aredescribed, for example, in:

Winnacker-Küchler, “Chemische Technologie” [Chemical Engineering],Volume 7, C. Hauser Verlag Munich, 4th Ed. 1986; van Falkenberg,“Pesticides Formulations”, Marcel Dekker N.Y., 2nd Ed. 1972-73; K.Martens, “Spray Drying Handbook”, 3rd Ed. 1979, G. Goodwin Ltd. London.

The formulation auxiliaries required, such as inert materials,surfactants, solvents and other additives are also known and aredescribed, for example, in:

Watkins, “Handbook of Insecticide Dust Diluents and Carriers”, 2nd Ed.,Darland Books, Caldwell N.J.; H. v. Olphen, “Introduction to ClayColloid Chemistry”, 2nd Ed., J. Wiley & Sons, N.Y.; Marsden, “SolventsGuide”, 2nd Ed., Interscience, N.Y. 1950; McCutcheon's, “Detergents andEmulsifiers Annual”, MC Publ. Corp., Ridgewood N.J.; Sisley and Wood,“Encyclopedia of Surface Active Agents”, Chem. Publ. Co. Inc., N.Y.1964; Schönfeldt, “Grenzflächenaktive Äthylenoxidaddukte”[Surface-active ethylene oxide adducts], Wiss. Verlagsgesell., Stuttgart1967; Winnacker-Küchler, “Chemische Technologie” [Chemical Engineering],Volume 7, C. Hauser Verlag Munich, 4th Ed.1986.

Based on these formulations, it is also possible to prepare combinationswith other pesticidally active substances, fertilizers and/or growthregulators, for example in the form of a ready mix or a tank mix.Wettable powders are preparations which are uniformly dispersible inwater and which, beside the active substance, also comprise wettingagents, for example polyoxyethylated alkylphenols, polyoxyethylatedfatty alcohols, alkyl- or alkylphenolsulfonates and dispersants, e.g.sodium lignosulfonate and sodium 2,2′-dinaphthylmethane6,6′-disulfonate,in addition to a diluent or inert substance. Emulsifiable concentratesare prepared by dissolving the active substance in an organic solvent,for example butanol, cyclohexanone, dimethylformamide, xylene, or elsehigher-boiling aromatics or hydrocarbons with addition of one or moreemulsifiers. Emulsifiers which can be used are for example: calciumalkylarylsulfonates, such as calcium dodecylbenzenesulfonate, ornonionic emulsifiers such as, for example, fatty acid polyglycol esters,alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propyleneoxide/ethylene oxide condensates, alkyl polyethers, sorbitan fatty acidesters, polyoxyethylene sorbitan fatty acid esters or polyoxyethylenesorbitol esters.

Dusts are obtained by grinding the active substance with finely dividedsolid substances, for example talc, natural clays such as kaolin,bentonite, pyrophyllite or diatomaceous earth. Granules can be preparedeither by spraying the active substance onto adsorptive granulated inertmaterial or by applying active substance concentrates to the surface ofcarriers such as sand, kaolinites or granulated inert material with theaid of binders, for example polyvinyl alcohol, sodium polyacrylate orelse mineral oils. Suitable active substances can also be granulated inthe manner customary for the preparation of fertilizer granules, ifdesired in a mixture with fertilizers.

In wettable powders, the active substance concentration is, for example,approximately 10 to 90% by weight, the remainder to 100% being composedof customary formulation components. In the case of emulsifiableconcentrates, the active substance concentration can amount toapproximately 5 to 80% by weight. Formulations in the form of dustsusually comprise 5 to 20% by weight of active substance, sprayablesolutions approximately 2 to 20% by weight. In the case of granules, theactive substance content depends partly on whether the active compoundis in liquid or solid form and on which granulation auxiliaries, fillersand the like are being used.

Additionally, the abovementioned formulations of active substancescomprise, if appropriate, the tackifiers, wetting agents, dispersants,emulsifiers, penetrants, solvents, fillers or carriers which arecustomary in each case.

For use, the concentrates which are in commercially available form are,if appropriate, diluted in the customary manner, for example by means ofwater in the case of wettable powders, emulsifiable concentrates,dispersions and in some cases also microgranules. Preparations in theform of dusts and granules and sprayable solutions are usually notdiluted further with other inert substances prior to use.

The rate of application required varies with the external conditionssuch as, inter alia, temperature and humidity. It can vary within widelimits, for example between 0.0005 and 10.0 kg/ha or more activesubstance, but it is preferably between 0.001 and 5 kg/ha.

The active substances according to the invention can be present in theircommercially available formulations and in the use forms prepared fromthese formulations in the form of mixtures with other active substances,such as insecticides, attractants, sterilants, acaricides, nematicides,fungicides, ovicides, growth regulators or herbicides.

The pesticides include, for example, phosphoric esters, carbamates,carboxylic esters, formamidines, tin compounds, substances produced bymicroorganisms and the like.

Preferred components for mixtures are:

1. from the group of the phosphorus compounds acephate, azamethiphos,azinphosethyl, azinphosmethyl, bromophos, bromophosethyl,chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl,demeton, demeton-S-methyl, demeton-S-methylsulfone, dialifos, diazinon,dichlorvos, dicrotophos, O,O-1,2,2,2-tetrachloroethylphosphorothioate(SD 208 304), dimethoate, disulfoton, EPN, ethion, ethoprophos,etrimfos, famphur, fenamiphos, fenitriothion, fensulfothion, fenthion,fonofos, formothion, heptenophos, isozophos, isothioate, isoxathion,malathion, methacrifos, methamidophos, methidathion, salithion,mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl,parathion, parathion-methyl, phenthoate, phorate, phosalone, phosfolan,phosmet, phosphamidon, phoxim, pirimiphos, pirimiphos-ethyl,pirimiphos-methyl, profenofos, propaphos, proetamphos, prothiofos,pyraclofos, pyridapenthion, quinalphos, sulprofos, temephos, terbufos,tetrachlorvinphos, thiometon, triazophos, trichlorphon, vamidothion;

2. from the group of the carbamates aldicarb, 2-sec-butylphenylmethylcarbamate (BPMC), carbaryl, carbofuran, carbosulfan, cloethocarb,benfuracarb, ethiofencarb, furathiocarb, isoprocarb, methomyl,5-methyl-m-cumenyl butyryl(methyl)carbamate, oxamyl, pirimicarb,propoxur, thiodicarb, thiofanox, ethyl4,6,9-triaza4-benzyl-6,10-dimethyl-8-oxa-7-oxo-5,11-dithia-9-dodecenoate(OK 135),1-methylthio(ethylideneamino)-N-methyl-N-(morpholinothio)carbamate (UC51717);

3. from the group of the carboxylic esters allethrin, alphametrin,5-benzyl-3-furylmethyl (E)-(1R)-cis,2,2-dimethyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate,bioallethrin, bioallethrin ((S) cyclopentyl isomer), bioresmethrin,biphenate, (RS)-1-cyano-1-(6-phenoxy-2-pyridyl)methyl(1RS)-trans-3-(4-tert-butylphenyl)-2,2-dimethylcyclopropanecarboxylate(NCI 85193), cycloprothrin, cyhalothrin, cythithrin, cypermethrin,cyphenothrin, deltamethrin, empenthrin, esfenvalerate, fenfluthrin,fenpropathrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (Disomer), permethrin, pheothrin ((R)-isomer), d-pralethrin, pyrethrins(natural products), resmethrin, tefluthrin, tetramethrin, tralomethrin;

4. from the group of the amidines amitraz, chlordimeform;

5. from the group of the tin compounds cyhexatin, fenbutatinoxide;

6. others abamectin, Bacillus thuringiensis, bensultap, binapacryl,bromopropylate, buprofezin, camphechlor, cartap, chlorobenzilate,chlorfluazuron, 2-(4-chlorophenyl)-4,5-diphenylthiophene (UBI-T 930),chlorfentezine, 2-naphthylmethyl cyclopropanecarboxylate (Ro12-0470),cyromazin, ethylN-(3,5-dichloro4-(1,1,2,3,3,3-hexafluoro-1-propyloxy)phenyl)carbamoyl)-2-chlorobenzocarboximidate,DDT, Dicofol,N-(N-(3,5-dichloro4-(1,1,2,2-tetrafluoroethoxy)phenylamino)carbonyl)-2,6-difluorobenzamide(XRD 473), diflubenzuron,N-(2,3-dihydro-3-methyl-1,3-thiazol-2-ylidene)-2,4-xylidine, dinobuton,dinocap, endosulfan, ethofenprox,(4-ethoxyphenyl)(dimethyl)(3-(3-phenoxyphenyl)propyl)silane,(4-ethoxyphenyl)(3-(4-fluoro-3-phenoxyphenyl)propyl)dimethylsilane,fenoxycarb, 2-fluoro-5-(4-(4-ethoxyphenyl)-4-methyl-1-pentyl) diphenylether (MTI 800), granulosis and nuclear polyhedrosis viruses,fenthiocarb, flubenzimine, flucycloxuron, flufenoxuron, gamma-HCH,hexythiazox, hydramethylnon (AC 217300), ivermectin,2-nitromethyl-4,5-dihydro-6H-thiazine (DS 52618),2-nitromethyl-3,4-dihydrothiazole (SD 35651),2-nitromethylene-1,2-thiazinan-3-ylcarbamaldehyde (WL 108477),propargite, teflubenzuron, tetradifon, tetrasul, thiocyclam, trifumuron,imidacloprid.

The active substance content of the use forms prepared from thecommercially available formulations can range from 0.00000001 to 95% byweight of active substance, it is preferably between 0.00001 and 1% byweight.

They are applied in a customary manner adapted to the use forms.

The active substances according to the invention are also suitable forcontrolling endo- and ectoparasites in the field of veterinary medicineand in the field of animal keeping.

The active substances according to the invention are applied by oraladministration, for example in the form of tablets, capsules, drinks,granules, by dermal administration, for example by dipping, spraying,pouring-on and spotting-on and dusting, and also by parenteraladministration, for example by means of an injection, e.g. s.c.

Accordingly, the novel compound of the formula I according to theinvention can also be employed especially advantageously in livestockkeeping (for example cattle, sheep, pigs and poultry such as chickens,geese, and the like). In a preferred embodiment of the invention, thenovel compounds are administered orally to the animals, if appropriatein the form of suitable formulations (cf. above) and if appropriatetogether with the drinking water or feed. Since elimination with thefeces is efficient, this enables simple prevention of the development ofinsects in the animals' feces. The dosages and formulations which aresuitable in each case depend, in particular, on the species and thedevelopmental stage of the productive livestock and also on the degreeof infection and can be readily determined and established by thecustomary methods. In the case of cattle, the novel compounds can beemployed for example at dosages of from 0.01 to 1 mg/kg bodyweight.

The compounds of the formula I according to the invention are alsodistinguished by an outstanding fungicidal activity. Fungal pathogenswhich have already penetrated the plant tissue can be controlledsuccessfully in a curative fashion. This is especially important andadvantageous in the case of those fungal diseases which can no longer becontrolled efficiently with the otherwise customary fungicides onceinfection has set in. The spectrum of action of the claimed compoundsincludes a variety of economically important phytopathogenic fungi suchas, for example, Plasmopara viticola, Phytophthora infestans, Erysiphegraminis, Pyricularia oryzae, Pyrenophora teres, Leptosphaeria nodorumund Pellicularia sasakii and Puccinia recondita.

The compounds according to the invention are in addition also suitablefor use in industrial fields, for example as wood preservatives, aspreservatives in paints, in cooling lubricants for metalworking, or aspreservatives in drilling and cutting oils.

The active substances according to the invention can be used in theircommercially available formulations either alone or in combination withother fungicides known from the literature.

Fungicides known from the literature which can be combined in accordancewith the invention with the compounds of the formula I are, for example,the following products:

aldimorph, andoprim, anilazine, BAS 480F, BAS 450F, BAS 490F, benalaxyl,benodanil, benomyl, binapacryl, bitertanol, bromuconazole, buthiobate,captafol, captan, carbendazim, carboxin, CGA 173506, cyprodinil,cyprofuram, dichlofluanid, dichlomezin, diclobutrazol, diethofencarb,difenconazole (CGA 169374), difluconazole, dimethirimol, dimethomorph,diniconazole, dinocap, dithianon, dodemorph, dodine, edifenfos,ethirimol, etridiazole, epoxiconazole, fenbuconazole, fenarimol,fenfuram, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate,fentin hydroxide, ferimzone (TF164), fluazinam, fluobenzimine,fludioxinil, fluquinconazole, fluorimide, flusilazole, flutolanil,flutriafol, folpet, fosetyl-aluminum, fuberidazole, fulsulfamide (MT-F651), furalaxyl, furconazole, furmecyclox, guazatine, hexaconazole, ICIA5504, imazalil, imibenconazole, iprobenfos, iprodione, isoprothiolane,KNF 317, copper compounds such as copper oxychloride, oxine-copper,copper oxide, mancozeb, maneb, mepanipyrim (KIF 3535), metconazol,mepronil, metalaxyl, methasulfocarb, methfuroxam, MON 24000,myclobutanil, nabam, nitrothalidopropyl, nuarimol, ofurace, oxadixyl,oxycarboxin, penconazole, pencycuron, PP 969, probenazole, propineb,prochloraz, procymidon, propamocarb, propiconazole, prothiocarb,pyracarbolid, pyrazophos, pyrifenox, pyrimethanil, pyroquilon,rabenzazole, RH7592, sulfur, tebuconazole, TF 167, thiabendazole,thicyofen, thiofanatemethyl, thiram, tolclofos-methyl, tolylfluanid,triadimefon, triadimenol, triazoxide, tricyclazole, tridemorph,triflumizole, triforine, trifionazol, validamycin, vinchlozolin, XRD563, zineb, sodium dodecylsulfonate, sodium dodecyl sulfate, sodiumC13/C15-alcohol ether sulfonate, sodium cetostearyl phosphate ester,sodium dioctylsulfosuccinate, sodium isopropylnaphthalenesulfonate,sodium methylenebisnaphthalenesulfonate, cetyltrimethylammoniumchloride, salts of long-chain primary, secondary or tertiary amines,alkylpropyleneamines, laurylpyrimidinium bromide, ethoxylatedquaternized fatty amines, alkyldimethylbenzylammonium chloride and1-hydroxyethyl-2-alkyl-imidazoline.

The abovementioned components in combinations are known activesubstances, many of which are described in Ch.R Worthing, S. B. Walker,The Pesticide Manual, 7th edition (1983), British Crop ProtectionCouncil. The active substance content of the use forms prepared from thecommercially available formulations can vary within wide ranges, theactive substance concentration of the use forms can amount to from0.0001 to 95% by weight of active substance, it is preferably between0.0001 and 1% by weight. They are applied in a customary manner adaptedto suit the use forms.

The examples which follow are intended to illustrate the inventionwithout imposing any limitation thereto.

A. Formulation Examples

a) A dust was obtained by mixing 10 parts by weight of active substanceand 90 parts by weight of talc as inert substance and comminuting themixture in a hammer mill.

b) A wettable powder which was readily dispersible in water was obtainedby mixing 25 parts by weight of active substance, 65 parts by weight ofkaolin-containing quartz as inert substance, 10 parts by weight ofpotassium lignosulfonate and 1 part by weight of sodiumoleoylmethyltaurinate as wetting agent and dispersant and grinding themixture in a pinned-disk mill.

c) A dispersion concentrate which is readily dispersible in water wasprepared by mixing 40 parts by weight of active substance with 7 partsby weight of a sulfosuccinic monoester, 2 parts by weight of a sodiumlignosulfosuccinate and 51 parts by weight of water and grinding themixture in a ball mill to a fineness of below 5 microns.

d) An emulsifiable concentrate was prepared from 15 parts by weight ofactive substance, 75 parts by weight of cyclohexane as solvent and 10parts by weight of oxyethylated nonylphenol (10 EO) as emulsifier.

e) Granules were prepared from 2 to 15 parts by weight of activesubstance and an inert carrier material for granules such asattapulgite, pumice granules and/or quartz sand. Expediently, asuspension of the wettable powder from Example b) with a solids contentof 30% was used; this was sprayed onto the surface of attapulgitegranules and the latter were dried and mixed intimately. The wettablepowder amounted to approximately 5% by weight and the inert carriermaterial to approximately 95% of the finished granules.

B. Preparation Examples EXAMPLE A

4-(6-Ethoxytetralin-2-yloxy)quinazoline

2.57 g (13.3 mmol) of 6-ethoxytetralin-2-ol in 5 ml of THF were added,with ice-cooling, to a suspension of 400 mg of NaH (80% pure, 13.3 mmolin 40 ml of THF). The mixture was subsequently refluxed for 1 hour andcooled to room temperature, and 2.0 g (12.2 mmol) of 4-chloroquinazolinewere added. The mixture was refluxed for 24 hours and cooled and thendiluted with ether and washed with saturated sodium hydrogen carbonateand saturated sodium chloride solution. After the organic phase had beendried and concentrated, the residue was chromatographed on silica gelusing petroleum ether/ethyl acetate (9:1, 8:2). This gave 2.39 g (61% oftheory) of colorless crystals (m.p.115-117° C.).

Preparation of 6-ethoxytetralin-2-ol

1.97 g (52 mmol) of sodium borohydride were added in portions of 0° C.to 9.8 g (51.4 mmol) of 6-ethoxy-2-tetralone in 150 ml of ethanol. Themixture was stirred for 1 hour at 0° C. and diluted with 200 ml of 2Nsodium hydroxide solution, and the solution was extracted withdichloromethane. The combined organic phases were washed with saturatedsodium chloride solution, dried and concentrated. This gave 9.8 g of anoil which was further reacted without purification.

Preparation of 6-ethoxy-2-tetralone

39.1 g (0.20 mol) of 4-ethoxyphenylacetyl chloride in 200 ml ofdichloromethane were added dropwise in the course of 1 hour at −78° C.to 53.4 g (0.4 mol) of aluminum chloride in 800 ml of dichloromethane. Avigorous stream of ethylene was subsequently passed in in the course of15 minutes, and the mixture was allowed to come to room temperature andstirred for a further 3 hours. The dark red solution was cooled to 0° C.and carefully treated with 300 ml of ice-water. After phase separation,the organic phase was washed with 2N HCl (3×) and saturated sodiumhydrogen carbonate solution, dried and evaporated on a rotaryevaporator. After purification by column chromatography with petroleumether/ethyl acetate (9:1, 8:2), 20.9 g (56% of theory) of a yellow syrupwere obtained.

Preparation of 4-ethoxyphenylacetyl chloride

50 g (0.28 mol) of 4-ethoxyphenylacetic acid were treated with 50 ml ofthionyl chloride and the mixture was stirred for 24 hours at roomtemperature. Excess thionyl chloride was removed in vacuo and theresidue was distilled under a high vacuum. This gave 39 g (71% oftheory) of an oil (boiling point 110° C./53.3 Pa).

EXAMPLE B

5-Chloro-6-ethyl-4-(6-methoxytetralin-2-ylamino)pyrimidine

1.5 g (8.5 mmol) of 4,5-dichloro-6-ethylpyrimidine, 1.5 g (8.5 mmol) of2-amino-6-methoxytetralin and 2 ml of triethylamine were heated for 10hours at 85° C. The mixture was subsequently diluted with water andether, the phases were separated, and the organic phase was washed withwater and saturated NaCl solution. After the mixture had been dried andconcentrated, the residue was purified by column chromatography withpetroleum ether/ethyl acetate (8:1). This gave 2.4 g (89% of theory) ofcolorless crystals (melting point 70-71° C.).

Preparation of 2-amino-6-methoxytetralin

6.0 g (30 mmol) of 2-azido-6-methoxytetralin 15 ml of TMF were addeddropwise in the course of 15 minutes at 0° C. to a suspension of 1.7 g(44 mmol) of lithium aluminum hydride in 70 ml of THF. The mixture wasstirred for 30 minutes at room temperature and refluxed for 1 hour.After cooling to 0° C., excess alanate was destroyed with isopropanol,and the mixture was diluted with ether and washed with saturatedtartrate and saturated NaCl solution. After the organic phase had beendried and concentrated, the resulting colorless oil was further employeddirectly. Yield 5.1 g (96% of theory).

Preparation of 2-azido-6-methoxytetralin

8.0 g (31 mmol) of 2-methanesulfonyloxy-6-methoxytetralin and 2.6 g (40mmol) of sodium azide were heated for 3 hours at 90° C. in 100 ml ofDMF. After the mixture had been cooled, it was diluted with ether,washed with water and saturated NaCl solution, dried and concentrated invacuo. This gave 6 g (95% of theory) of a colorless oil which wasfurther reacted directly.

Preparation of 2-methanesulfonyloxy-6-methoxytetralin

4.5 g (39 mmol) of methanesulfonyl chloride were added dropwise at 0° C.to a solution of 5.4 g (30 mmol) of 6-methoxytetralin-2-ol and 4.6 g (45mmol) of triethylamine in 60 ml of dichloromethane. The mixture wasstirred for 1 hour at 0° C. and then washed with water, 2N HCl,saturated NaHCO₃ solution and saturated NaCl solution. After the mixturehad been dried and concentrated, 8 g (97% of theory) of mesylate wereobtained, and this was further reacted without purification.

EXAMPLE C

5-Chloro-6-ethyl-4-(6-hydroxytetralin-2-ylamino)pyrimidine

A solution of 5.8 g (18 mmol) of5-chloro6-ethyl4-(6-methoxytetralin-2-ylamino)pyrimidine in 22 ml of 48%HBr and 4.5 ml of acetic acid was heated for 4 hours at 110° C. Afterthe mixture had cooled, it was brought to pH=8 with sodium hydroxidesolution and extracted with dichloromethane. After the dichloromethanephase had been dried, concentrated and washed with toluene, 4.8 g (88%of theory) of colorless crystals were obtained (m.p. 178° C.).

EXAMPLE D

5-Chloro-6-ethyl-4-(6-trifluoromethylsulfonyloxytetralin-2-ylamino)pyrimidine

1.55 g (5.5 mmol) of trifluoromethanesulfonyl anhydride were added at 0°C. to a solution of 1.2 g (4.0 mmol) of5-chloro-6-ethyl-4-(6-hydroxytetralin-2-ylamino)pyrimidine in 5 ml ofpyridine. The mixture was stirred for 2 hours at room temperature,diluted with dichloromethane and washed with saturated NaHCO₃ solution.After the dichloromethane phase had been dried, concentrated andpurified by column chromatography with petroleum ether/ethyl acetate(7:3), 1.0 g (57% of theory) of a colorless oil were obtained.

The compounds of the tables which follow were obtained analagously toExamples A to D:

TABLE 1

Ex. m.p. No. R² R³ X Z R⁴ R⁵ [° C.] 1 C₂H₅ Cl NH CH₂ H H 2 CH₃OCH₂ OCH₃NH CH₂ H H 135-137 3 C₂H₅ Cl O CH₂ H H 4 CH₃OCH₂ OCH₃ O CH₂ H H 5 C₂H₅Cl NH O H H 6 CH₃OCH₂ OCH₃ NH O H H 152-153 7 CH₃OCH₂ OCH₃ NH S H H142-144 8 C₂H₅ Cl O S H H 9 C₂H₅ Cl NH S CH₃ CH₃ 135 10  C₂H₅ Cl O S CH₃CH₃

TABLE 2

Ex. m.p. No. R² R³ X R⁴ R⁵ [° C.] 11 C₂H₅ Cl O H H 85 12 C₂H₅ Cl NH H H13 CH₃OCH₂ OCH₃ O H H 48 14 CH₃OCH₂ OCH₃ NH H H 101-103 15 (CH)₄ O H H59 16 (CH)₄ NH H H 17 (CH₂)₄ O H H 110 18 (CH₂)₄ NH H H 19 C₂H₅ Cl NHOCH₃ H 20 (CH)₄ NH OCH₃ H 21 (CH)₄ O OCH₃ H 22 C₂H₅ Cl NH OC₂H₅ H 23C₂H₅ Cl NH OCH₂O

TABLE 3

Ex. m.p. No. R² R³ X R⁴ R⁵ [° C.] 24 C₂H₅ Cl O H H oil 25 C₂H₅ Cl NH H H26 CH₃OCH₂ OCH₃ O H H oil 27 CH₃OCH₂ OCH₃ NH H H 28 (CH)₄ O H H 119-12129 (CH)₄ NH H H 30 (CH₂)₄ O H H oil 31 (CH₂)₄ NH H H 32 C₂H₅ Cl O OCH₃ H33 C₂H₅ Cl NH OCH₃ H 34 (CH)₄ O OCH₃ H 35 C₂H₅ Cl NH OC₂H₅ H 36 C₂H₅ ClNH OCH₂O

TABLE 4

Ex. m.p. No. R² R³ X R⁴ R⁵ R⁶ [° C.] 37 C₂H₅ Cl O H H H oil 38 C₂H₅ ClNH H H H 80-82 39 CH₃OCH₂ OCH₃ O H H H oil 40 CH₃OCH₂ OCH₃ NH H H H115-116 41 (CH)₄ O H H H 75 42 (CH)₄ NH H H H 43 CF—(CH)₃ O H H H 44CCl—(CH)₃ O H H H 45 (CH₂)₄ O H H H oil 46 (CH₂)₄ NH H H H 47 C₂H₅ Cl OH H OCH₃ 45-48 48 C₂H₅ Cl NH H H OCH₃ 70-71 49 CH₃OCH₂ OCH₃ O H H OCH₃oil 50 CH₃OCH₂ OCH₃ NH H H OCH₃ oil 51 (CH)₄ O H H OCH₃ 114-115 52 (CH)₄NH H H OCH₃ 165-166 53 CF—(CH)₃ NH H H OCH₃ 200 54 CF—(CH)₃ O H H OCH₃55 (CH₂)₄ O H H OCH₃ 87-88 56 C₂H₅ Cl O H H OC₂H₅ 64-67 57 C₂H₅ Cl NH HH OC₂H₅ 100 58 CH₃OCH₂ OCH₃ O H H OC₂H₅ oil 59 CH₃OCH₂ OCH₃ NH H H OC₂H₅oil 60 (CH)₄ O H H OC₂H₅ 115-117 61 (CH)₄ NH H H OC₂H₅ 62 CF(CH)₃ O H HOC₂H₅ 104 63 CCl(CH)₃ O H H OC₂H₅ 126-128 64 (CH₂)₄ O H H OC₂H₅ 65 C₂H₅Cl O H H OH 66 C₂H₅ Cl NH H H OH 178 67 (CH)₄ O H H OH 68 C₂H₅ O H HO-n-C₂H₇ 69 C₂H₅ NH H H O-n-C₃H₇ 70 (CH)₄ O H H O-n-C₃H₇ 71 (CH)₄ NH H HO-n-C₃H₇ 72 C₂H₅ Cl O H H O-i-C₃H₇ 73 C₂H₅ Cl NH H H O-i-C₃H₇ oil 74(CH)₄ O H H O-i-C₃H₇ oil 75 (CH)₄ NH H H O-i-C₃H₇ 147 76 CF(CH)₃ O H HO-i-C₃H₇ oil 77 CF(CH)₃ NH H H O-i-C₃H₇ 187 78 CCl(CH)₃ NH H H O-i-C₃H₇133 79 C₂H₅ H O H H O-i-C₃H₇ oil 80 C₂H₅ Cl O H H O—CH₂(C₂H₃) 81 C₂H₅ ClNH H H O—CH₂(C₂H₃) 82 (CH)₄ O H H O—CH₂(C₂H₃) 94 83 CF(CH)₃ O H HO—CH₂(C₂H₃) 84 C₂H₅ Cl O H H O—CH₂(C₂H₃) 85 C₂H₅ Cl NH H H O—CH₂(C₂H₃)86 (CH)₄ O H H O—CH₂(C₂H₃) 72 87 CF(CH)₃ O H H O—CH₂(C₂H₃) 88 C₂H₅ Cl NHH H O-s-C₄H₉ oil 89 C₂H₅ Cl O H H O-s-C₄H₉ 90 (CH)₄ NH H H O-s-C₄H₉ 18591 (CH)₄ O H H O-s-C₄H₉ 92 CF(CH)₃ NH H H O-s-C₄H₉ 108 93 CF(CH)₃ O H HO-s-C₄H₉ 94 C₂H₅ H O H H O-s-C₄H₉ oil 95 C₂H₅ Cl NH H H O-t-C₄H₉ oil 96C₂H₅ Cl NH H H OC₂H₄OCH₃ 97 C₂H₅ Cl O H H OC₂H₄OCH₃ oil 98 (CH)₄ NH H HOC₂H₄OCH₃ 99 (CH)₄ O H H OC₂H₄OCH₃ oil 100  C₂H₅ Cl O H H O-benzyl 67101  C₂H₅ Cl NH H H O-benzyl 102  (CH)₄ O H H O-benzyl 89 103  CF(CH)₃ OH H O-benzyl 118 104  CCl(CH)₃ O H H O-benzyl 119 105  C₂H₅ Cl O H H4-NO₂-phenoxy 98 106  (CH)₄ O H H 4-NO₂-phenoxy 149 107  CF(CH)₃ O H H4-NO₂-phenoxy 153 108  (CH)₄ O H H 2-NO₂-phenoxy oil 109  C₂H₅ Cl O H H4-Cl-phenoxy oil 110  (CH)₄ O H H 4-Cl-phenoxy oil 111  C₂H₅ Cl NH H H4-CF₃-phenoxy oil 112  C₂H₅ Cl NH H H pyridin-2-yloxy oil 113  C₂H₅ ClNH H H 5-CF₃-pyridin-2-yloxy 95 114  C₂H₅ Cl NH H H 3-CN-pyridin-2-yloxy188 115  C₂H₅ Cl NH H H pyrimidin-2-yloxy 100 116  (CH)₄ O H H CMF₂ oil117  C₂H₅ O H H OCF₂CF₂Br oil 118  (CH)₄ O H H OCF₂CF₂Br oil 119 CF(CH)₃ O H H OCF₂CF₂Br 87 120  C₂H₅ Cl NH H H OCH₂CO₂-t-C₄H₉ oil 121 C₂H₅ Cl NH H H OCO₂C₂H₅ 96 122  C₂H₅ Cl NH H H OCONHCH₃ 210 123  C₂H₅ ClO H H OCON(CH₃)₂ 124  C₂H₅ Cl NH H H OCON(CH₃)₂ 129 125  C₂H₅ Cl NH H HOCONMEt 180 126  C₂H₅ Cl NH H H OCONEt₂ 93 127  C₂H₅ Cl NH H HOCO—N-pyrrolidinyl 150 128  C₂H₅ Cl NH H H OCO—N-morpholinyl 159 129 C₂H₅ Cl NH H H OCONHcyclo-hexyl 186 130  C₂H₅ Cl NH H H OCONH-t-butyl126 131  C₂H₅ Cl NH H H OCON-(i-propyl)₂ 132  C₂H₅ Cl O H H OCONHC₆H₅133  C₂H₅ Cl NH H H OCONHC₆H₅ 140 134  (CH)₄ O H H OCON(CH₃)C₆H₅ 135 C₂H₅ Cl NH H H OCON(CH)₃C₆H₅ 146 136  C₂H₅ Cl O H H OSO₂CH₃ oil 137 C₂H₅ Cl NH H H OSO₂CH₃ oil 138  (CH)₄ O H H OCO₂CH₃ 139  CF(CH)₃ O H HOCO₂CH₃ 173 140  C₂H₅ Cl O H H OSO₂C₃H₇ 141  C₂H₅ Cl NH H H OSO₂C₃H₇ oil142  C₂H₅ Cl O H H OSO₂CF₃ 143  C₂H₅ Cl NH H H OSO₂CF₃ oil 144  (CH)₄ OH H OSO₂N(CH₃)₂ oil 145  C₂H₅ Cl O H H F 96 146  (CH)₄ O H H F 93 147 C₂H₅ Cl NH H H Cl 125-126 148  CH₃OCH₂ OCH₃ NH H H Cl 131-132 149 CH₃OCH₂ OCH₃ O H H Cl 150  C₂H₅ Cl O H H Br 151  (CH)₄ O H H Br 125 152 C₂H₅ Cl O H H CN 107 153  (CH)₄ O H H CN 125 154  CF(CH)₃ O H H CN 160155  CCl(CH)₃ O H H CN 200 156  C₂H₅ Cl O H H CONH₂ 148 157  (CH)₄ O H HCONH₂ 175 158  CF(CH)₃ O H H CONH₂ 210 159  (CH)₄ O H H CONHC₆H₅ oil160  (CH)₄ O H H COOCH₃ oil 161  C₂H₅ Cl O H H COCH₃ oil 162  (CH)₄ O HH COCH₃ 104 163  C₂H₅ Cl NH H H OPO(OEt)₂ oil 164  C₂H₅ Cl NH H HOPS(OCH₃)₂ oil 165  C₂H₅ Cl NH H H CH₃ 166  C₂H₅ Cl NH H H i-C₃H₇ oil167  C₂H₅ Cl O H H i-C₃H₇ oil 168  (CH)₄ NH H H i-C₃H₇ 166 169  (CH)₄ OH H i-C₃H₇ 170  CF(CH)₃ O H H i-C₃H₇ oil 171  C₂H₅ H O H H i-C₃H₇ oil172  C₂H₅ Cl NH H OCH₃ H 173  (CH)₄ NH H O-i-C₃H₇ H oil

TABLE 5

Ex. m.p. No. R² R³ R⁴ R⁵ R⁶ R⁷ [° C.] 174 C₂H₅ Cl H H H H oil 175CH₃OCH₂ OCH₃ H H H H 111 176 (CH)₄ H H H H 231 177 C₂H₅ Cl H CH₃ H H 73178 CH₃OCH₂ OCH₃ H CH₃ H H 106 179 C₂H₅ Cl OCH₃ H OCH₃ H 64 180 C₂H₅ ClOCH₃ H H H 181 C₂H₅ Cl H H H OCH₃ 182 C₂H₅ Cl H C₂H₅ H H 183 C₂H₅ Cl H HOSO₂CH₃ H 184 C₂H₅ Cl H H OSO₂CF₃ H 185 C₂H₅ Cl H H OSO₂CF₃ H 186 C₂H₅Cl H H OCON(CH₃)₂ H 187 C₂H₅ Cl H H OSO₂C₃H₇ H

C. Biological Examples

Use as fungicide

The activity of the preparations according to the invention was assessedusing a 0-4 scale, in which

0 means a disease suppression of 0-24%

1 means a disease suppression of 25-49%

2 means a disease suppression of 50-74%

3 means a disease suppression of 75-97%

4 means a disease suppression of 97-100%.

EXAMPLE F

Barley plants cv. “Maris Otter” in the 2-leaf stage were sprayed torun-off with a solution of the compound according to the invention in amixture of 40% of acetone and 60% of water. 24 hours later, the plantswere inoculated with conidia of powdery mildew of barley (Erysiphegraminis f. sp. hordei) and kept in a controlled-environment cabinet at20° C. and a relative atmospheric humidity of 75-80%. 7 days after thetreatment, the plants were examined for symptoms of powdery mildew ofbarley. The following compounds scored 3 or 4 at 500 mg of activesubstance/l spray mixture:

Compounds of Examples No. 58, 60, 61 and 148.

EXAMPLE G

Tomato plants cv.“First in the Field” in the 3-4-leaf stage were sprayedto run-off with a solution of the compound according to the invention ina mixture of 40% of acetone and 60% of water. 24 hours later, the plantswere inoculated with a spore suspension of Phytophthora infestans(20,000 spores/ml) and kept in a controlled-environment cabinet at 15°C., first for 2 days at a relative atmospheric humidity of 99% and thenfor 4 days at a relative atmospheric humidity of 75-80%. 6 days afterthe treatment, the plants were examined for symptoms of Phytophthorainfestans. The following compounds scored 3 or 4 at 500 mg of activesubstance/l spray mixture:

Compounds of Examples No. 49, 52, 56 and 148.

EXAMPLE H

Grapevine seedlings cv.“Grüner Veltliner” approximately 6 weeks old weresprayed to run-off with a solution of the compound according to theinvention in a mixture of 40% of acetone and 60% of water. 24 hourslater, the plants were inoculated by spraying with a zoospore suspension(100,000/ ml) of Plasmopara viticola and kept in acontrolled-environment cabinet at 70° C. and a relative atmospherichumidity of approximately 99%. 14 days after the treatment, the plantswere examined for symptoms of Plasmopara viticola. The followingcompounds scored 3 or 4 at 500 mg of active substance/l spray mixture:

Compounds of Examples No. 48, 49, 52, 53, 56, 57, 59, 60, 61, 62, 64,73, 75, 76, 77, 82, 86, 88, 90, 92, 97, 99, 100, 102, 103, 104, 106,108, 112, 113, 114, 118, 121, 124, 126, 128, 131, 133, 136, 137, 139,140, 141, 154, 155, 158, 159, 160, 161, 166, 168, 170, 171, 177 and 179.

EXAMPLE I

Wheat plants cv. “Hornet” in the 2-leaf stage were sprayed to run-offwith a solution of the compound according to the invention in a mixtureof 40% of acetone and 60% of water. 24 hours later, the plants wereinoculated by spraying with a pyknospore suspension (500,000/ml) ofLeptosphaeria nodorum and kept in a controlled-environment cabinet at18-20° C. and a relative atmospheric humidity of approximately 99%. 14days after inoculation, the plants were examined for symptoms ofLeptosphaeria nodorum. The following compounds scored 3 or 4 at 500 mgof active substance/l spray mixture:

Compounds of Examples No. 52, 53, 60, 62, 73, 75, 77, 78, 79, 86, 88,90, 92, 94, 99, 100, 102, 103, 106, 107, 108, 110, 111, 113, 115, 119,122, 125, 126, 130, 131, 133, 135, 139, 141, 143, 144, 148, 157, 158,159, 166, 167, 168 and 176.

EXAMPLE K

Rice plants cv. “Nihonbare” in the 1.5-leaf stage were sprayed torun-off with a solution of the compound according to the invention in amixture of 40% of acetone and 60% of water. A solution of the substancein a mixture of 5% of acetone and 95% of water was appliedsimultaneously by pouring. 24 hours later, the plants were inoculated byspraying with a pyknospore suspension (10⁶/ml) of Pyricularia oryzae.The plants were kept for 2 days in a darkened controlled-environmentcabinet at 26° C. and a relative atmospheric humidity of 99% andsubsequently transferred into an illuminated controlled-environmentcabinet at approximately 18° C. and a relative atmospheric humidity of75-80%. 7-9 days after inoculation, the plants were examined forsymptoms of Pyricularia oryzae. The following substances scored 3 or 4at 500 mg of active substance/l spray mixture:

Compounds of Examples No. 48, 49, 57, 58, 60, 61, 66, 73, 74, 76, 78,82, 94, 97, 99, 100, 102, 103, 104, 109, 110, 112, 113, 114, 116, 118,119, 126, 128, 136, 139, 141, 143, 144, 151, 160, 167, 168, 170, 171,174, 175, 176, 177 and 179.

EXAMPLE L

Apple seedlings (Malus sp.) approximately 3 weeks old were sprayed torun-off with a solution of the compound according to the invention in amixture of 40% of acetone and 60% of water. After 24 hours, the plantswere inoculated by spraying with a spore suspension (300,000/ml) ofVenturia inaequalis. The plants were kept for 2 days in the dark at18-20° C. and a relative atmospheric humidity of 99%, subsequently inthe light for 5 days at the same atmospheric humidity and finally for 7days at an atmospheric humidity of 75-80%. 14 days after the treatment,the plants were examined for symptoms of Venturia inaequalis. Thefollowing substances scored 3 or 4 at 500 mg of active substance/l ofspray mixture:

Compounds according to Examples No. 73, 174 and 175.

EXAMPLE M

Tomato plants cv. “First in the Field” in the 2-3-leaf stage weresprayed to run-off with a solution of the compound according to theinvention in a mixture of 40% of acetone and 60% of water. After 24hours, the plants were inoculated with a spore suspension (500,000/ml)of Botrytis cinerea. The plants were kept in a controlled-environmentcabinet at 18-20° C. and a relative atmospheric humidity of 99%. 5 daysafter inoculation, the plants were examined for symptoms of Botrytiscinerea. The following substances scored 3 or 4 at 500 mg of activesubstance/l spray mixture:

Compounds of Examples No. 73 and 175.

EXAMPLE N

Wheat cv. “Jubilar” in the 2-leaf stage was treated to run-off withaqueous suspensions of the claimed compounds. After the spray coatinghad dried on, the plants were inoculated with an aqueous sporesuspension of Puccinia recondita. The plants, treated to run-off, wereplaced for approximately 16 hours into a controlled-environment cabinetat 20° C. and an atmospheric humidity of approximately 100%. They werethen grown on in a greenhouse at a temperature of 22 to 25° C. and arelative atmospheric humidity of 50 to 70%. After an incubation time ofapproximately 2 weeks, the fungus sporulated on the entire leaf surfaceof the untreated control plants (infection level 100%) so that it waspossible to assess the disease level of the test plants. The diseaselevel was expressed in % diseased leaf area in comparison with theuntreated control plants, which showed an infection level of 100%. Thefollowing compounds scored 3 or 4 at 500 mg of active substance/l spraymixture:

Compounds of Examples No. 13, 14, 38, 39, 40, 48 and 50.

Use as insecticide/acaricide

EXAMPLE O

Portions of 1 ml of the test formulation, emulsified in water, wereapplied uniformly to the insides of the dish and of the cover of a Petridish and, after the coating had dried on, batches of 10 imagines of thecommon housefly (Musca domestica) were introduced. After the dishes hadbeen closed, they were kept at room temperatures, and the mortality ofthe test animals was determined after 3 hours. At 300 ppm (activesubstance content in the test solution), the preparations of ExamplesNo. 50, 57, 59, 73, 124, 137 and 179 showed 100% mortality of the testanimals which had been introduced.

EXAMPLE P

Rice seeds were germinated on cotton wool in glass culture dishes undermoist conditions and, after they had grown to a stem length ofapproximately 8 cm, were introduced with the leaves into the testsolution. After the solution had run off, the treated rice plants wereintroduced into culture containers separately for each testconcentration and populated with batches of 10 larvae (L3) of thespecies Nilaparvata lugens. After the sealed culture containers had beenkept at 21° C., the mortality of the leafhopper larvae was determinedafter 4 days. At a concentration of 300 ppm (active substance content inthe test solution), 100% mortality of the test animals introduced wasshown by the preparations of Examples No. 59, 61, 73, 137, 141, 179,111, 95, 166, 126, 97 and 99.

EXAMPLE Q

Wheat seed was pregerminated for 6 hours under water and thentransferred into 10 ml glass test tubes and covered with 2 ml of soil ineach case. After 1 ml of water had been added, the plants remained inthe culture tubes at room temperature (21° C.) until they had reached aplant height of approximately 3 cm. Diabrotica undecimpunctata larvae inthe middle stage (batches of 10) were subsequently introduced onto thesoil in the glass tubes and, after 2 hours, 1 ml of the test liquid inthe concentration to be tested was pipetted onto the soil surface in theglass tubes. After they had been left to stand for 5 days underlaboratory conditions (21° C.), soil and roots were examined for liveDiabrotica larvae and the mortality was determined. At 300 ppm (activesubstance content in the test solution), 100% mortality of the testanimals which had been introduced was shown by the preparations ofExamples No. 57, 59, 61, 73, 124, 137, 95 and 53.

EXAMPLE R

Field beans (Vicia faba) which were severely populated with the blackbean aphid (Aphis fabae) were sprayed with aqueous dilutions of wettablepowder concentrates with an active substance content of 300 ppm to thestage of beginning run-off. The mortality of the aphids was determinedafter 3 days. A 100% destruction was achieved with the compounds ofExamples No. 14, 48, 57, 73, 124, 137, 143, 179, 126, 112 and 163.

EXAMPLE S

Bean plants (Phaseolus v.) which were severely infested with greenhousered spider mites (Tetranychus urticae, full population) were sprayedwith the aqueous dilution of a wettable powder concentrate whichcontained 300 ppm of the active substance in question. The mortality ofthe mites was checked after 7 days. 100% destruction was achieved withthe compounds of Examples No. 57, 73, 137, 141, 95, 166, 126, 112 and163.

Use as ovicide

EXAMPLE T

Filter paper disks supporting eggs of large milkweed bugs (Oncopeltusfasciatus) were each treated with 0.5 ml portions of aqueous dilution ofthe test formulation. After the coating had dried on, the Petri dish wasclosed and the inside was kept at maximum atmospheric humidity. Afterthe dishes had been kept at room temperature, the ovicidal activity wasdetermined after 7 days. At an active substance content of 300 ppm, 100%ovicidal activity was achieved by the compounds of Examples No. 13, 14,15, 38, 39, 40, 48, 52, 57, 59, 61, 73, 124, 137, 147, 174, 175 and 179.

EXAMPLE U

L2 larvae of Spodoptera littoralis (Egyptian cotton leafworm) wereintroduced into Petri dishes, the dishes having been equipped at thebottom with filter paper and containing a small amount of nutrientmedium. The dishes with the nutrient medium and the larvae which hadbeen introduced were sprayed with the aqueous emulsions of the testsubstances, and the Petri dishes were closed with a cover. After 5 daysat approximately 23° C., the activity of the compound against the larvaewas determined. A 100% activity was achieved with the compounds ofExamples No. 57 and 124 at a concentration of 300 ppm (active compoundcontent) in the spray mixture.

Use as antiparasitic

EXAMPLE V

In-vitro test on tropical cattle ticks (Boophilus microplus)

The activity of the compounds according to the invention against tickswas demonstrated in the following experimental set-up: To produce asuitable preparation of active substance, the active substances weredissolved at a concentration of 10% (w/v) in a mixture composed ofdimethylformamide (85 g), nonylphenol polyglycol ether (3 g) andoxyethylated castor oil (7 g) and the resulting emulsion concentrateswere diluted with water to a test concentration of 500 ppm.

Batches of ten female tropical ticks, Boophilus microplus, which hadsucked themselves full were immersed for five minutes in these dilutionsof active substance. The ticks were subsequently dried on filter paperand then attached, with their backs, to an adhesive film in order todeposit eggs. The ticks were kept in an incubator at 28° C. and anatmospheric humidity of 90%.

For the control, female ticks were immersed in water only. The activitywas assessed on the basis of the inhibition of egg deposition two weeksafter the treatment. In this test, the compounds of Examples No. 56, 57,59, 60, 179, 112, 163, 115, 113 and 111 caused in each case 100%inhibition of egg deposition.

What is claimed is:
 1. A compound of formula I

in which R¹ is hydrogen, halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl or(C₃-C₅)-cycloakyl; R₂ and R₃ are identical or different and are in eachcase hydrogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₂-C₄)-alkenyl,(C₂-C₄)-haloalkenyl, (C₂-C₄)-alkynyl, (C₂-C₄) -haloalkynyl,tri-(C₁-C₄)-alkylsilyl-(C₂-C₄)-alkynyl, (C₁-C₄)-alkoxy,(C₁C₄)-haloalkoxy, (C₁-C₄)-alkoxy-(C₁C₄)-alkyl,(C₁-C₄)-haloalkoxy-(C₁-C₄)-alkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-haloalkyl,(C₁-C₄)-haloalkoxy-(C₁-C₄)-haloalkyl, halogen, hydroxyl,(C₁-C₄)-hydroxyalkyl, (C₁-C₄)-alkanoyl, (C₁-C₄)-alkanoyl-(C₁-C₄)-alkyl,(C₂-C₄)-haloalkanoyl, (C₃-C₅)-cycloalkyl, (C₄-C₅)-cycloalkenyl,(C₃-C₅)-cycloalkoxy, (C₃-C₅)-halocycloalkyl, (C₄-C₅)-halocycloalkenyl,cyano, (C₁-C₄)-cyanoalkyl, nitro, (C₁-C₄)-nitroalkly, thiocyano,(C₁-C₄)-thiocyanoalkyl, (C₁-C₄)-alkoxycarbonyl,(C₁-C₄)-alkoxycarbonyl-(C₁-C₄)-alkyl, (C₁-C₄)-haloalkoxycarbonyl,(C₁-C₄)-alkanoyloxy-(C₁-C₄)-alkyl, (C₁-C₄)-alkylthio,(C₁-C₄)-alkylthio-(C₁-C₄)-alkyl, (C₁-C₄)haloalkylthio,(C₁-C₄)-alkylsulfinyl, (C₁-C₄)-haloalkylsulfinyl, (C₁-C₄)- or(C₁-C₄)-haloalkylsulfonoyl; A is N; X is NH, O or S(O)_(q) where q is 0,1 or 2; Y¹Y² and Y³ independently of one another are a group of heformula —O—, —CO—, —CNR⁶—, —S(O)_(r)—, —N(O)₁R⁶— or CR⁷R⁸ where r is 0,1 or 2 and 1 is 0 or 1 or Y¹ or Y³ replace a direct bond; R⁴ is hydrogenof (C₁-C₄)-alkyl; m is 0or 1; n is 0, 1, 2, 3 or 4; Z is a direct bond,NR⁹, O, S(O)_(s) where s is 0, 1 or 2, OSO₂, SO₂O, NR¹⁰SO₂, SO₂NR ¹¹,SiR¹²R¹³, U¹P(W¹)V¹V² or

 where U¹, U² in dependently of one another are direct bond, NR¹⁴ or O;W¹, W² independently of one another are oxygen or sulfur; V¹, V², V³independently of one another a direct bond, NR¹⁵ or oxygen, where R⁹,R¹⁰, R¹¹, R¹⁴ and R¹⁵ are identical or different and are in each casehydrogen alkyl, alkoxy, alkanoyl or cycloalkyl; R⁵ radicals aresubstituents which are independent of one another and are halogen,cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl and itbeing possible for one or more non-adjacent saturated carbon units inthe last-mentioned 5 radicals to be replaced by a carbonyl group or byoxygen, S(O)_(x) where x is 0, 1 or 2, NR¹⁶ or SiR¹⁷R¹⁸, and whereinthese last-mentioned 5 radicals, with or without the above mentionedvariations, are optionally substituted by one or more, in the case offluorine up to the maximum number of identical or different radicalsD¹R¹⁹, or R⁵ is aryl or heterocyclyl, it being possible for these tworadicals to be unsubstituted or to be substituted by up to three, in thecase of fluorine also up to the maximum number of, identical ordifferent radicals D²R²⁰, or two adjacent radicals Z—R⁵ together withthe carbon atoms to which they are attached can form a fused cyclehaving 4 to 6 ring atoms which is carbocyclic or contains hetero ringatoms selected from the group consisting of O, S and N and which isunsubstituted of substituted by one or more radicals selected from thegroup consisting of halogen, (C₁-C₄)-alkyl and oxo, or R⁶, R¹⁰, R¹¹ orR¹⁵ independently of one another together with the R⁵ which is attachedto Z can be form a 4- to 8-membered ring system in which one or two CH₂groups are optionally replaced by oxygen, S(O)_(t) where t is 0, 1 or 2or NR²⁵, where R⁶ is hydrogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,(C₂-C₄)-alkenyl, (C₂-C₄)-haloalkenyl, (C₂-C₄)-alkynyl,(C₂-C₄)-haloalkynyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy,(C₁C₄)-alkythio, (C₁-C₄)-haloalkylthio, (C₁-C₄)-alkanoyl,(C₂-C₄)-haloalkanoyl, (C₃-C₅)-cycloalkyl, (C₁-C₄,)-alkylsulfonyl,(C₁-C₄)haloalkylsulfonyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,(C₁-C₄)-alkoxycarbonyl; R⁷ and R⁸ independently of one another arehydrogen, hydroxyl, halogen, cyano, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,(C₂-C₄)-alkenyl, (C₂-C₄)-haloalkenyl, (C₂-C₄)-alkynyl,(C₂-C₄)-haloalkenyl, (C₃-C₅)-cycloalkyl, (C₁-C₄)-alkanoyl,(C₁-C₄)-haloalkanoyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy,(C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio or (C₁-C₄)-haloalkylthio; R¹² andR¹³ independently of one another are (C₁-C₄)-alkyl or phenyl; R¹⁶ ishydrogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy or (C₁-C₄)-alkanoyl; R¹⁷ and R¹⁸independently of one another are (C₁-C₄)-alkyl, D¹ and D² are in eachcase independent of one another and are a direct bond, oxygen, S(O)_(k),SO₂O, OSO₂, CO, OCO, COO, NR²¹, SO₂NR²¹, NR²¹SO₂, ONR²¹, NR²¹O NR²¹CO,CONR²¹ or SiR²²R²³ and k is 0, 1 or 2, where R²¹ radicals independentlyof one another are hydrogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkanoyl or(C₃-C₅)-cycloalkyl; R²² and R²³ independently of one another are(C₁-C₄)-alkyl; R¹⁹ and R²⁰ independently of one another are hydrogen,cyano, nitro, halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl,haloalkynl, alkoxyalkyl, haloalkoxyalkyl, alklylthioalkyl,haloalkylthioalkyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl,cycloalkenylalkyl, aryl, heterocyclyl, aryalkyl or heterocyclyalkyl, thecycloalipathic, aromatic or heterocyclic ring systems in thelast-mentioned 8 radicals being unsubstituted or substituted or with oneto three, in the case of fluorine also up to the maximum number of,identical or different substituents R²⁴, or R¹⁹ and R²⁰, attached to thesame carbon atom, together are an oxo group; where R²⁴ radicalsindependently of one another are (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,(C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, cyano, nitro or halogen; R²⁵independently of one another are hydrogen, (C₁-C₈)-alkyl,(C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-alkylthio,(C₃-C₅)-cycloalkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-alkynyl, (C₁-C₄)-alkanoyl,(C₁-C₄)-haloalkanoyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, phenyl-(C₁-C₄)-alkylor phenyl, the phenyl groups independently of one another beingunsubstituted or being provided with up to three, in the case offluorine also up to the maximum number of, identical or differentsubstituents R²⁶, where R²⁶ substituents independently of one anotherare (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-alkylthio,halogen or cyano, or a salt thereof.
 2. A compound of the formula I asclaimed in claim 1 in which R¹ is hydrogen, halogen, (C₁-C₄)-alkyl,(C₁-C₄)-haloalkyl or (C₃-C₅)-cycloalkyl; R² and R³ are identical ordifferent and are in each case hydrogen, (C₁-C₄)-alkyl,(C₁-C₄)-haloalkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-haloalkenyl,(C₂-C₄)-alkynyl, (C₂-C₄)-haloalkynyl,tri-(C₁-C₄)-alkylsilyl-(C₂-C₄)-alkynyl, (C₁-C₄)-alkoxy,(C₁-C₄)-haloalkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,(C₁-C₄)-haloalkoxy-(C₁-C₄)-alkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-haloalkyl,(C₁-C₄)-haloalkoxy-(C₁-C₄)-haloalkyl, halogen, hydroxyl,(C₁-C₄)-hydroxyalkyl, (C₁-C₄)-alkanoyl, (C₁-C₄)-alkanoyl-(C₁-C₄)-alkyl,(C₂-C₄)-haloalkanoyl, (C₃-C₅)-cycloalkyl, (C₄-C₅)-cycloalkenyl,(C₃-C₅)-cycloalkoxy, (C₃-C₅)-halocycloalkyl, (C₄-C₅)-halocycloalkenyl,cyano, (C₁-C₄)-cyanoalkyl, nitro, (C₁-C₄)-nitroalkyl, thiocyano,(C₁-C₄)-thiocyanoalkyl, (C₁-C₄)-alkoxycarbonyl,(C₁-C₄)-alkoxycarbonyl-(C₁-C₄)-alkyl, (C₁-C₄)-haloalkoxycarbonyl,(C₁-C₄)-alkanoyloxy-(C₁-C₄)-alkyl, (C₁-C₄)-alkylthio,(C₁-C₄)-alkylthio-(C₁-C₄)-alkyl, (C₁-C₄)-haloalkylthio,(C₁-C₄)-alkylsulfinyl, (C₁-C₄)-haloalkylsulfinyl, (C₁-C₄)-alkylsulfonylor (C₁-C₄)-haloalkylsulfonyl; A is N; X is NH, O or S(O)_(q) where q is0, 1 or 2; Y¹, Y² and Y³ independently of one another are a group of theformula —O—, —S(O)_(r)—, —N(O)_(l)R⁶— or CR⁷R⁸ where r is =0, 1 or 2 andl is 0 or 1; or Y¹ or Y³ replace a direct bond; Ry⁴ is hydrogen or(C₁-C₄)-alkyl; m is 1; n is 1 or 2; Z is a direct bond, NR⁹, O, S(O)_(s)where s is 0, 1 or 2, OSO₂, SO₂O, NR¹⁰SO₂, SO₂NR¹¹, SiR¹²R¹³,U¹P(W¹)V¹V² or

 where U¹, U² independently of one another are a direct bond, NR¹⁴ or O;W¹, W² independently of one another are oxygen or sulfur; V¹, V², V³independently of one another are a direct bond, NR¹⁵ or oxygen, whereR⁹, R¹⁰, R¹¹, R¹⁴ and R¹⁵ are identical or different and are in eachcase hydrogen, alkyl, alkoxy, alkanoyl or cycloalkyl; R⁵ radicals aresubstitutents which are independent of one another and are halogen,cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl andwhere up to three non-adjacent saturated carbon units in thelast-mentioned 5 radicals are replaced by a carbonyl group or by oxygen,S(O)_(x) where x is 0, 1 or 2, NR¹⁶ or SiR¹⁷R¹⁸,and where thelast-mentioned 5 radicals, with or without the abovementionedvariations, are optionally substituted by one to three, in the case offluorine up to the maximum number of, identical or different radicalsD¹R¹⁹, or R⁵ is aryl or heterocyclyl, where these two radicals areoptionally substituted by one to three, in the case of fluorine also upto the maximum number of, identical or different radicals D²R²⁰, or twoadjacent radicals Z—R⁵ together with the carbon atoms to which they areattached form a fused cycle having 4 to 6 ring atoms which iscarbocyclic or contains hetero ring atoms selected from the groupconsisting of O, S and N and which is unsubstituted or substituted byone or more radicals selected from the group consisting of halogen,(C₁-C₄)-alkyl and oxo, or R⁹, R¹⁰, R¹¹, R¹⁴ or R¹⁵ independently of oneanother together with the R⁵ which is attached to Z form a 4- to8-membered ring system in which a CH₂ group is optionally replaced byoxygen, S(O)_(t) where t is 0, 1 or 2 or NR²⁵, where R⁶ is hydrogen,(C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-haloalkenyl,(C₂-C₄)-alkynyl, (C₂-C₄)-haloalkynyl, (C₁-C₄)-alkoxy,(C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-haloalkylthio,(C₁-C₄)-alkanoyl, (C₂-C₄)-haloalkanoyl, (C₃-C₅)-cycloalkyl,(C₁-C₄)-alkylsulfonyl, (C₁-C₄)-haloalkylsulfonyl,(C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₄)-alkoxycarbonyl; R⁷ and R⁸independently of one another are hydrogen, hydroxyl, halogen, cyano,(C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-haloalkenyl,(C₂-C₄)-alkynyl, (C₂-C₄)-haloalkenyl, (C₃-C₅)-cycloalkyl,(C₁-C₄)-alkanoyl, (C₁-C₄)-haloalkanoyl, (C₁-C₄)-alkoxy,(C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio or (C₁-C₄)-haloalkylthio; R¹² andR¹³ are methyl; R¹⁶ is hydrogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy or(C₁-C₄)-alkanoyl; R¹⁷ and R¹⁸ are methyl; D¹ and D² are in each caseindependent of one another and are a direct bond, oxygen, S(O)_(k),SO₂O, OSO₂, CO, OCO, COO, NR²¹, SO₂NR²¹, NR²¹SO₂, ONR²¹, NR²¹O, NR²¹CO,CONR²¹ or SiR²²R²³ and k is 0, 1 or 2, where R²¹ radicals independentlyof one another are hydrogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkanoyl or(C₃-C₅)-cycloalkyl; R²² and R²³ independently of one another are(C₁-C₄)-alkyl; R¹⁹ and R²⁰ independently of one another are hydrogen,cyano, nitro, halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl,haloalkynyl, alkoxyalkyl, haloalkoxyalkyl, alkylthioalkyl,haloalkylthioalkyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl,cycloalkenylalkyl, aryl, heterocyclyl, arylalkyl or heterocyclyalkyl,the cycloaliphatic, aromatic or heterocyclic ring systems inlast-mentioned 8 radicals are unsubstituted or substituted with one tothree, in the case of fluorine also up to the maximum number of,identical or different substituents R²⁴, or R¹⁹ and R²⁰, attached to thesame carbon atom, together are an oxo group; where R²⁴ radicalsindependently of one another are (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,(C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, cyano, nitro or halogen; R²⁵independently of one another are hydrogen, (C₁-C₈)-alkyl,(C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-alkylthio,(C₃-C₅)-cycloalkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-alkynyl, (C₁-C₄)-alkanoyl,(C₁-C₄)-haloalkanoyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, phenyl-(C₁-C₄)-alkylor phenyl, the phenyl groups independently of one another areunsubstituted or substituted with one to three, in the case or fluorinealso up to the maximum number of, identical or different substituentsR²⁶, where R²⁶ substituents independently of one another are(C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-alkylthio,halogen or cyano, or a salt thereof.
 3. A compound of the formula I asclaimed in claim 1 in which R⁵ radicals are substituents which areindependent of one another and are halogen, cyano, nitro,(C₁-C₂₀)-alkyl; (C₂-C₂₀)-alkenyl, (C₂-C₂₀)-alkynyl, (C₃-C₈)-cycloalkyl,(C₄-C₈)-cycloalkenyl and one or more non-adjacent saturated carbon unitsin the last-mentioned 5 radicals are optionally replaced by a carbonylgroup or by oxygen, S(O)_(x) where x is 0, 1 or 2, NR¹⁶ or SiR¹⁷R¹⁸ andwherein these last mentioned 5 radicals, with or without theabovementioned variations, are optionally substituted by one or more, inthe case of fluorine up to the maximum number of identical or differentradicals D¹R¹⁹, or R⁵ is aryl or heterocyclyl, wherein these tworadicals are unsubstituted or substituted one to three, in the case offluorine also up to the maximum number of, identical or differentradicals D²R²⁰, or two adjacent radicals R⁹, R¹¹ or R¹⁵ independently ofone another together with the R⁵ attached to Z form a 4- to 8-memberedring system in which one or two CH₂ groups are replaced by oxygen,S(O)_(t) where t is 0, 1 or 2 or NR²⁵, where R¹⁶ is hydrogen,(C₁-C₄)-alkyl, (C₁-C₄)-alkoxy or (C₁-C₄)-alkanoyl; R¹⁷ and R¹⁸independently of one another are (C₁-C₄)-alkyl; D¹ and D² are in eachcase independent of one another and are a direct bond, oxygen, S(O)_(k),SO₂O, OSO₂, CO, OCO, COO, NR²¹, SO₂NR²¹, NR²¹SO₂, ONR²¹, NR²¹O, NR²¹CO,CONR²¹ or SiR²²R²³ and k is 0, 1 or 2, where R²¹ radicals independentlyof one another are hydrogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkanoyl or(C₃-C₅)-cycloalkyl; R²² and R²³ independently of one another are(C₁-C₄)-alkyl; R¹⁹ and R²⁰ independently of one another are hydrogen,cyano, nitro, halogen, (C₁-C₈)-alkyl, (C₁-C₈)-haloalkyl,(C₂-C₈)-alkenyl, (C₂-C₈)-haloalkenyl, (C₂-C₈)-alkynyl,(C₂-C₈)-haloalkynyl, (C₁-C₈)-alkoxy-(C₁-C₄)-alkyl,(C₁-C₈)-haloalkoxy-(C₁-C₄)-alkyl, (C₁-C₈)-alkylthio-(C₁-C₄)-alkyl,(C₁-C₈)-haloalkylthio-(C₁-C₄)-alkyl, (C₃-C₈)-cycloalkyl,(C₄-C₈)-cycloalkenyl, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkyl,(C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkyl, aryl, heterocyclyl,aryl-(C₁-C₄)-alkyl or heterocyclyl-(C₁-C₄)-alkyl, where, in thelast-mentioned 8 radicals, the cycloaliphatic aromatic or heterocyclicring systems are unsubstituted or substituted one to three, in the caseof fluorine also up to the maximum number of, identical or differentsubstituents R²⁴, or R¹⁹ and R²⁰, attached to the same carbon atom,together are an oxo group, where R²⁴ radicals independently of oneanother are (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy,(C₁-C₄)-haloalkoxy, cyano, nitro or halogen; R²⁵ radicals are hydrogen,(C₁-C₈)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-alkylthio,(C₃-C₅)-cycloalkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-alkynyl, (C₁-C₄)-alkanoyl,(C₂-C₄)-haloalkanoyl, (C₂-C₄)-alkoxyalkyl, phenyl-(C₁-C₄)-alkyl orphenyl and the phenyl groups independently of one another areunsubstituted or substituted one to three, in the case of fluorine alsoup to the maximum number of, identical or different substituents R²⁶,where R²⁶ radicals independently of one another are (C₁-C₄)-alkyl,(C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-alkylthio, halogen or cyano,or a salt thereof.
 4. A compound of the formula I as claimed in claim 1where R⁵ radicals are substituents which are independent of one anotherand are halogen, cyano, nitro, (C₁-C₂₀)-alkyl, (C₂-C₂₀)-alkenyl,(C₂-C₂₀)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl and up tothree non-adjacent saturated carbon units in the last-mentioned 5radicals are optionally replaced by a carbonyl group or by oxygen,S(O)_(x) where x is 0, 1 or 2, NR¹⁶ or SiR¹⁷R¹⁸ and wherein theselast-mentioned 5 radicals, with or without the abovementionedvariations, are optionally substituted by one to three, in the case offluorine up to the maximum number of, identical or different radicalsD¹R¹⁹, or R⁵ is aryl or heterocyclyl, wherein these two radicals to beunsubstituted or to be substituted by one to three, in the case offluorine also up to the maximum number of, identical or differentradicals D²R²⁰, or two adjacent radicals Z—R⁵ together with the carbonatoms to which they are attached form a fused cycle having 4 to 6 ringatoms which is carbocyclic or contains hetero ring atoms selected fromthe group consisting of O, S and N and which is unsubstituted orsubstituted by one or more radicals selected from the group consistingof halogen, (C₁-C₄)-alkyl and oxo, or R⁹, R¹¹ or R¹⁵ independently ofone another together with the R⁵ attached to Z form a 4- to 8-memberedring system in which one CH₂ group is replaced by oxygen, S(O)_(t) wheret is 0, 1 or 2 or NR²⁵, where R¹⁶ is hydrogen, (C₁-C₄)-alkyl,(C₁-C₄)-alkoxy or (C₁-C₄)-alkanoyl; R¹⁷ and R¹⁸ are methyl; D¹ and D²are in each case independent of one another and are a direct bond,oxygen, S(O)_(k), SO₂O, OSO₂, CO, OCO, COO, NR²¹, SO₂NR²¹, NR²¹SO₂,ONR²¹, NR²¹O, NR²¹CO, CONR²¹ or SiR²²R²³ and k is 0, 1 or 2, where R²¹radicals independently of one another are hydrogen, (C₁-C₄)-alkyl,(C₁-C₄)-alkanoyl or (C₃-C₅)-cycloalkyl; R²² and R²³ independently of oneanother are (C₁-C₄)-alkyl; R¹⁹ and R²⁰ independently of one another arehydrogen, cyano, nitro, halogen, (C₁-C₈)-alkyl, (C₁-C₈)-haloalkyl,(C₂-C₈)-alkenyl, (C₂-C₈)-haloalkenyl, (C₂-C₈)-alkynyl,(C₂-C₈)-haloalkynyl, (C₁-C₈)-alkoxy-(C₁-C₄)-alkyl,(C₁-C₈)-haloalkoxy-(C₁-C₄)-alkyl, (C₁-C₈)-alkylthio-(C₁-C₄)-alkyl,(C₁-C₈)-haloalkylthio-(C₁-C₄)-alkyl, (C₃-C₈)-cycloalkyl,(C₄-C₈)-cycloalkenyl, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkyl,(C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkyl, aryl, heterocyclyl,aryl-(C₁-C₄)-alkyl or heterocyclyl-(C₁-C₄)-alkyl, where, in thelast-mentioned 8 radicals the cvcloaliphatic, aromatic or heterocyclicring systems are unsubstituted or substituted one to three, in the caseof fluorine also up to the maximum number of, identical or differentsubstituents R²⁴, or R¹⁹ and R²⁰, attached to the same carbon atom,together are an oxo group, where R²⁴ radicals independently of oneanother are (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy,(C₁-C₄)-haloalkoxy, cyano, nitro or halogen; R²⁵ radicals areindependently of one another hydrogen, (C₁-C₈)-alkyl, (C₁-C₄)-haloalkyl,(C₁-C₄)-alkoxy, (C₁-C₄)-alkylthio, (C₃-C₅)-cycloalkyl, (C₂-C₄)-alkenyl,(C₂-C₄)-alkynyl, (C₁-C₄)-alkanoyl, (C₂-C₄)-haloalkanoyl,(C₂-C₄)-alkoxyalky, phenyl-(C₁-C₄)-alkyl or phenyl and the phenyl groupsare unsubstituted or substituted one to three, in the case of fluorinealso up to the maximum number of, identical or different substituentsR²⁶, where R²⁶ radicals independently of one another are (C₁-C₄)-alkyl,(C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-alkylthio, halogen or cyano,or a salt thereof.
 5. A compound of the formula I as claimed in claim 1where R¹ is hydrogen, chlorine or fluorine; R² is (C₁-C₄)-alkyl,(C₂-C₄)-alkenyl, (C₂-C₄)-alkynyl,tri-(C₁-C₄)-alkylsilyl-(C₂-C₄)-alkynyl, (C₁-C₄)-haloalkyl, cyclopropyl,halocyclopropyl, methoxymethyl or cyano; R³ is hydrogen, halogen,methyl, ethyl, ethenyl, ethynyl, methoxy, ethoxy, cyano,trifluoromethyl, fluoromethylthio or methoxycarbonyl; A is N; X is NH oroxygen; Y¹, Y² and Y³ are a group of the formula —O—, —S(O)_(r)—,—N(O)_(I)R⁶— where I is 0 or 1 and where r is 0, 1 or 2, or are a groupof the formula CR⁷R⁸; or Y¹ or Y² replace a direct bond; R₄ is hydrogen;m is 1; n is 1 or 2; Z is a direct bond, NR⁹, O, S(O)_(s) where s is 0,1 or 2, or OSO₂, SO₂O, NR¹⁰SO₂, SO₂NR¹¹, SiR¹²R¹³, UP(W¹)V¹V² or

 where U¹, U² independently of one another are a direct bond, NR¹⁴ or O;W¹, W² are oxygen; V¹, V², V³ independently of one another are a directbond, NR¹⁵ or oxygen; where R⁶ radicals independently of one another are(C₁-C₄)-alkyl or (C₁-C₄)-alkanoyl; R⁷ and R⁸ independently of oneanother are hydrogen, halogen or (C₁-C₄)-alkyl, and R⁹, R¹⁰, R¹¹, R¹⁴and R¹⁵ are identical or different and are in each case hydrogen,(C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-alkanoyl or (C₃-C₅)-cycloalkyl,or a salt thereof.
 6. A compound of the formula I as claimed in claim 1where R¹ is hydrogen or fluorine; R² is methyl, ethyl, propyl,isopropyl, (C₁-C₂)-fluoroalkyl or methoxymethyl; R³ is halogen, methyl,ethyl, ethenyl, ethynyl, methoxy, ethoxy, trifluoromethyl,fluoromethylthio, methoxycarbonyl or cyano; A is N; X is NH or oxygen;Y¹, Y² and Y³ are a group of the formula —O—, or —S(O)_(r)—, where r is0, 1 or 2, or a group of the formula CR⁷R⁸, or Y¹ or Y³ replace a directbond, where R⁷ and R⁸ independently of one another are hydrogen ormethyl, or a salt thereof.
 7. Compound of the formula I as claimed inclaim 1 where R¹ is hydrogen; R² is ethyl, propyl, isopropyl,1-fluoroethyl or methoxymethyl; R³ is fluorine, chlorine, bromine,cyano, methoxy, ethenyl or ethynyl; or a salt thereof.
 8. A compound ofthe formula I as claimed in claim 1 where R¹ is hydrogen; R² is ethyl ormethoxymethyl; R³ is fluorine, chlorine, bromine or methoxy; R⁵ radicalsare substituents which are independent of one another and are halogen,cyano, nitro, (C₁-C₈)-alkyl, (C₂-C₈)-alkenyl, (C₂-C₈)-alkynyl,(C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl and wherein one to three,non-adjacent saturated carbon units in the last-mentioned 5 radicals areoptionally replaced by a carbonyl group or by oxygen, S(O)_(x) where xis 0, 1 or 2, NR¹⁶ or SiR¹⁷R¹⁸, and these last-mentioned 5 radicals,with or without the abovementioned variations, are optionallysubstituted by one to three, in the case of fluorine up to the maximumnumber of, identical or different radicals D¹R¹⁹, or R⁵ is aryl orheterocyclyl, wherein these two radicals are unsubstituted orsubstituted by one to three, in the case of fluorine also up to themaximum number of, identical or different radicals D²R²⁰, or twoadjacent radicals Z—R⁵ together with the carbon atoms to which they areattached form a fused cycle having 4 to 6 ring atoms which iscarbocyclic or contains hetero ring atoms selected from the groupconsisting of O, S and N and which is unsubstituted or substituted byone or more radicals selected from the group consisting of halogen,(C₁-C₄)-alkyl and oxo, or R¹¹ or R¹⁵ independently of one anothertogether with the R⁵ which is attached to Z form a 4- to 8-membered ringsystem in which one or two CH₂ groups, preferably one CH₂ group, arereplaced by hetero atom units such as oxygen, S(O)_(t) where t is 0, 1or 2 or NR²⁵, where R¹⁶ radicals independently of one another arehydrogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy or (C₁-C₄)-alkanoyl; R¹⁷ and R¹⁸independently of one another are (C₁-C₄)-alkyl; D¹ and D² are in eachcase independent of one another and are a direct bond, —O—, —S(O)_(k)—,—SO₂O—, —OSO₂—, —CO—, —OCO—, —COO—, —NR²¹—, —SO₂NR²¹—, —NR²¹SO₂—,—ONR²¹—, —NR²¹O—, —NR²¹CO—, —CONR²¹—, and k is 0, 1 or 2, and where R²¹radicals independently of one another are hydrogen, (C₁-C₄)-alkyl,(C₁-C₄)-alkanoyl or (C₃-C₅)-cycloalkyl; R¹⁹ and R²⁰ independently of oneanother are hydrogen, halogen, preferably fluorine, (C₁-C₈)-alkyl,(C₃-C₈)-cycloalkyl, aryl or heterocyclyl, the cycloaliphatic, aromaticor heterocyclic ring systems in the last-mentioned three radicals beingunsubstituted or substituted one to three, in the case of fluorine alsoup to the maximum number of, identical or different substituents R²⁴,where R²⁴ radicals independently of one another are (C₁-C₄)-alkyl,(C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, cyano, nitro orhalogen; R²⁵ radicals independently of one another are (C₁-C₈)-alkyl,(C₃-C₅)-cycloalkyl, (C₁-C₄)-alkanoyl, (C₂-C₄)-haloalkanoyl,(C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, phenyl-(C₁-C₄)-alkyl or phenyl and thephenyl groups independently of one another are unsubstituted orsubstituted one to three, in the case of fluorine also up to the maximumnumber of, identical or different substituents R²⁶, where R²⁶ radicalsindependently of one another are (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,(C₁-C₄)-alkoxy, (C₁-C₄)-alkylthio, halogen or cyano, or a salt thereof.9. A compound of the formula I as claimed in claim 1 where R⁵ is asdefined in claim 1 wherein one to three, non-adjacent saturated carbonunits are optionally replaced by oxygen and which, with or without theabovementioned variations, are optionally substituted by one to three,in the case of fluorine up to the maximum number of, identical ordifferent radicals D¹R⁹, or R⁵ is aryl or heterocyclyl, wherein thesetwo radicals are unsubstituted or substituted by one to three, in thecase of fluorine also up to the maximum number of, identical ordifferent radicals D²R²⁰, or a salt thereof.
 10. A compositioncomprising a compound as claimed in 1 and at least one formulationauxiliary.
 11. A method of controlling endo- or ectoparasites, whichcomprises administering such an amount of a compound as claimed in claim1 as is effective for this application.
 12. A method of controllingphytopathogenic fungi, which comprises applying a fungicidally activeamount of a compound as claimed in claim 1 to these phytopathogenicfungi or to the plants, areas or substrates infested with them, or toseed.
 13. A method of controlling insects, Acarina, molluscs, nematodesor eggs of these, which comprises applying an insecticidally,acaricidally, ixodicidally, nematicidally or ovicidally active amount ofa compound as claimed in claim 1 to these insects, Acarina, molluscs,nematodes or eggs of these or to the plants, areas or substratesinfested with them.